SCOPUS 정보 검색 플랫폼

Volumn 61, Issue 21, 1996, Pages 7426-7437

Synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides by reaction of 5′-protected nucleoside 2′,3′-dimesylates with telluride dianion: A general route from cis vicinal diols to olefins

(3) Clive, Derrick L J a Wickens, Philip L a Sgarbi, Paulo W M a

a UNIVERSITY OF ALBERTA (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; NUCLEOSIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029907726 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo9610570 Document Type: Article

Times cited : (45)

References (123)

1
- 0023091963
- (a) Mitsuya, H.; Broder, S. Nature 1987, 325, 773.
- (1987) Nature , vol.325 , pp. 773
- Mitsuya, H.¹ Broder, S.²

2
- 3643119053
- (b) De Clercq, E. AIDS/HIV Exp. Treatment Directory 1988, 2(2), 11.
- (1988) AIDS/HIV Exp. Treatment Directory , vol.2 , Issue.2 , pp. 11
- De Clercq, E.¹

3
- 0024393054
- (c) De Clerq, E.; Van Aerschot, A.; Herdewijn, P.; Baba, M.; Panwels, R.; Balzarini, J. Nucleosides Nucleotides 1989, 8, 659.
- (1989) Nucleosides Nucleotides , vol.8 , pp. 659
- De Clerq, E.¹ Van Aerschot, A.² Herdewijn, P.³ Baba, M.⁴ Panwels, R.⁵ Balzarini, J.⁶

4
- 0022552064
- (d) De Clercq, E. J. Med. Chem. 1986, 29, 1561.
- (1986) J. Med. Chem. , vol.29 , pp. 1561
- De Clercq, E.¹

5
- 85022357934
- July 4, 1994
- (a) FDA approval has been granted for AZT, DDC, DDI, and D4T: Chem. Eng. News 1994, 72(27), 22 (July 4, 1994).
- (1994) Chem. Eng. News , vol.72 , Issue.27 , pp. 22

6
- 0025947325
- 2 by OH: Beach, C. M.; Evans, R. K.; Coleman, M. S. Nucleosides Nucleotides 1991, 10, 1499.
- (1991) Nucleosides Nucleotides , vol.10 , pp. 1499
- Beach, C.M.¹ Evans, R.K.² Coleman, M.S.³

7
- 0000335222
- For a review on AIDS-driven nucleoside chemistry: Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
- (1992) Chem. Rev. , vol.92 , pp. 1745
- Huryn, D.M.¹ Okabe, M.²

8
- 0026598022
- Dueholm, K. L.; Pedersen, E. B. Synthesis 1992, 1.
- (1992) Synthesis , pp. 1
- Dueholm, K.L.¹ Pedersen, E.B.²

9
- 3643066973
- note
- In the case of the thymidine series, only 3′-deoxygenation would, of course, be needed.

10
- 0000146469
- N.Y.
- (a) Block, E. Org. React. (N.Y.) 1984, 30, 457.
- (1984) Org. React. , vol.30 , pp. 457
- Block, E.¹

11
- 0003543593
- VCH: New York
- (b) Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989; p 155.
- (1989) Comprehensive Organic Transformations
- Larock, R.C.¹

12
- 0001459506
- and references therein
- For more recent developments, see: (a) Liu, Z.; Classon, B.; Samuelsson, B. J. Org. Chem. 1990, 55, 4273 and references therein. (b) Luzzio, F. A.; Menes, M. E. J. Org. Chem. 1994, 59, 7267.
- (1990) J. Org. Chem. , vol.55 , pp. 4273
- Liu, Z.¹ Classon, B.² Samuelsson, B.³

13
- 0028600542
- For more recent developments, see: (a) Liu, Z.; Classon, B.; Samuelsson, B. J. Org. Chem. 1990, 55, 4273 and references therein. (b) Luzzio, F. A.; Menes, M. E. J. Org. Chem. 1994, 59, 7267.
- (1994) J. Org. Chem. , vol.59 , pp. 7267
- Luzzio, F.A.¹ Menes, M.E.²

14
- 0026596155
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1992) Nucleosides Nucleotides , vol.11 , pp. 787
- Dunkel, M.¹ Pfleiderer, W.²

15
- 0023726981
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1988) Synthesis , pp. 670
- Seela, F.¹ Muth, H.-P.² Bindig, U.³

16
- 0000903234
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1984) Tetrahedron Lett. , vol.25 , pp. 367
- Robins, M.J.¹ Hansske, F.² Low, N.H.³ Park, J.I.⁴

17
- 0027411541
- and references therein
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1993) Synthesis , pp. 303
- Talekar, R.R.¹ Coe, P.L.² Walker, R.T.³

18
- 0024409422
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1989) Nucleosides Nucleotides , vol.8 , pp. 699
- Nair, V.¹

19
- 84953491143
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1985) Synth. Commun. , vol.15 , pp. 401
- Prisbe, E.J.¹ Martin, J.C.²

20
- 0025335332
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1990) Tetrahedron Lett. , vol.31 , pp. 3829
- Lin, T.-S.¹ Yang, J.-H.² Liu, M.-C.³ Zhu, J.-L.⁴

21
- 0026553901
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1992) Nucleosides Nucleotides , vol.11 , pp. 373
- Yamaguchi, T.¹ Saneyoshi, M.²

22
- 0026598374
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1992) Synthesis , pp. 477
- Dorland, E.¹ Serafinowski, P.²

23
- 0024554252
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1989) J. Org Chem. , vol.54 , pp. 2217
- Chu, C.K.¹ Bhadti, V.S.² Doboszewski, B.³ Gu, Z.P.⁴ Kosugi, Y.⁵ Pullaiah, K.C.⁶ Van Roey, P.⁷

24
- 0025984290
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1991) Tetrahedron Lett. , vol.32 , pp. 7187
- Barton, D.H.R.¹ Jang, D.O.² Jaszberenyi, J.C.³

25
- 18544405790
- For recent examples of the preparation of 2′,3′-dideoxynucleosides from nucleosides, see: (a) Dunkel, M.; Pfleiderer, W. Nucleosides Nucleotides 1992, 11, 787. (b) Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367. (d) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303, and references therein. (e) Nair, V. Nucleosides Nucleotides 1989, 8, 699. (f) Prisbe, E. J.; Martin, J. C. Synth. Commun. 1985, 15, 401. (g) Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829. (h) Yamaguchi, T.; Saneyoshi, M. Nucleosides Nucleotides 1992, 11, 373. (i) Dorland, E.; Serafinowski, P. Synthesis 1992, 477. (j) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org Chem. 1989, 54, 2217. (k) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1991, 32, 7187. (l) Chen, B.-C.; Quinlan, S. L.; Stark, D. R.; Reid, J. G.; Audia, V. H.; George, J. G.; Eisenreich, E.; Brundidge, S. P.; Racha, S.; Spector, R. H. Tetrahedron Lett. 1995, 36, 7957.
- (1995) Tetrahedron Lett. , vol.36 , pp. 7957
- Chen, B.-C.¹ Quinlan, S.L.² Stark, D.R.³ Reid, J.G.⁴ Audia, V.H.⁵ George, J.G.⁶ Eisenreich, E.⁷ Brundidge, S.P.⁸ Racha, S.⁹ Spector, R.H.¹⁰

26
- 0024418643
- References 8j
- For an evaluation of some of the classical methods, see: (a) References 8j. (b) Mansuri, M. M.; Starrett, J. E., Jr.; Wos, J. A.; Tortolani, D. R.; Brodfuehrer, P. R.; Howell, H. G.; Martin, J. C. J. Org. Chem. 1989, 54, 4780.

27
- 0024418643
- For an evaluation of some of the classical methods, see: (a) References 8j. (b) Mansuri, M. M.; Starrett, J. E., Jr.; Wos, J. A.; Tortolani, D. R.; Brodfuehrer, P. R.; Howell, H. G.; Martin, J. C. J. Org. Chem. 1989, 54, 4780.
- (1989) J. Org. Chem. , vol.54 , pp. 4780
- Mansuri, M.M.¹ Starrett Jr., J.E.² Wos, J.A.³ Tortolani, D.R.⁴ Brodfuehrer, P.R.⁵ Howell, H.G.⁶ Martin, J.C.⁷

28
- 0027253071
- Preliminary communication: Clive, D. L. J.; Wickens, P. L. J. Chem. Soc., Chem. Commun. 1993, 923.
- (1993) J. Chem. Soc., Chem. Commun. , pp. 923
- Clive, D.L.J.¹ Wickens, P.L.²

29
- 37049114721
- Clive, D. L. J.; Denyer, C. V. J. Chem. Soc., Chem. Commun. 1973, 253.
- (1973) J. Chem. Soc., Chem. Commun. , pp. 253
- Clive, D.L.J.¹ Denyer, C.V.²

30
- 0041643947
- Clive, D. L. J.; Menchen, S. M. J. Org. Chem. 1980, 45, 2347.
- (1980) J. Org. Chem. , vol.45 , pp. 2347
- Clive, D.L.J.¹ Menchen, S.M.²

31
- 0000353895
- Dittmer, D. C.; Zhang, Y.; Discordia, R. P. J. Org. Chem. 1994, 59, 1004.
- (1994) J. Org. Chem. , vol.59 , pp. 1004
- Dittmer, D.C.¹ Zhang, Y.² Discordia, R.P.³

32
- 0025823632
- Recent reviews on the use of tellurium reagents: (a) Petragnani, N.; Comasseto, J. V. Synthesis 1991, 793. (b) Petragnani, N.; Comasseto, J. V. Synthesis 1991, 897. (c) Petragnani, N. Tellurium in Organic Synthesis; Academic Press: London, 1994.
- (1991) Synthesis , pp. 793
- Petragnani, N.¹ Comasseto, J.V.²

33
- 0025953937
- Recent reviews on the use of tellurium reagents: (a) Petragnani, N.; Comasseto, J. V. Synthesis 1991, 793. (b) Petragnani, N.; Comasseto, J. V. Synthesis 1991, 897. (c) Petragnani, N. Tellurium in Organic Synthesis; Academic Press: London, 1994.
- (1991) Synthesis , pp. 897
- Petragnani, N.¹ Comasseto, J.V.²

34
- 0003415425
- Academic Press: London
- Recent reviews on the use of tellurium reagents: (a) Petragnani, N.; Comasseto, J. V. Synthesis 1991, 793. (b) Petragnani, N.; Comasseto, J. V. Synthesis 1991, 897. (c) Petragnani, N. Tellurium in Organic Synthesis; Academic Press: London, 1994.
- (1994) Tellurium in Organic Synthesis
- Petragnani, N.¹

35
- 0345276359
- Suzuki, H.; Inouye, M. Chem. Lett. 1985, 225.
- (1985) Chem. Lett. , pp. 225
- Suzuki, H.¹ Inouye, M.²

36
- 0000638335
- Prince, M.; Bremer, B. W.; Brenner, W. J. Org. Chem. 1966, 31, 4292.
- (1966) J. Org. Chem. , vol.31 , pp. 4292
- Prince, M.¹ Bremer, B.W.² Brenner, W.³

37
- 0003514816
- Wiley: New York
- (a) Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis; Wiley: New York, 1967; p 662.
- (1967) Reagents for Organic Synthesis , pp. 662
- Fieser, L.F.¹ Fieser, M.²

38
- 33947294347
- (b) Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 35, 3195.
- (1970) J. Org. Chem. , vol.35 , pp. 3195
- Crossland, R.K.¹ Servis, K.L.²

39
- 0342910870
- Cf. Beels, C. M. D.; Coleman, M. J.; Taylor, R. J. K. Synlett 1990, 479.
- (1990) Synlett , pp. 479
- Beels, C.M.D.¹ Coleman, M.J.² Taylor, R.J.K.³

40
- 0025280171
- (a) Berridge, M. S.; Franceschini, M. P.; Rosenfeld, E.; Tewson, T. J. J. Org. Chem. 1990, 55, 1211. (b) Tewson, T. J. J. Org. Chem. 1983, 48, 3507. (c) Tewson, T. J.; Soderlind, M. J. Carbohydr. Chem. 1985, 4, 529. (d) Lowe, G.; Salamone, S. J. J. Chem. Soc., Chem. Commun. 1983, 1392. (e) Chai, C. L. L.; Hepburn, T. W.; Lowe, G. J. Chem. Soc., Chem. Commun. 1991, 1403. (f) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538. (g) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
- (1990) J. Org. Chem. , vol.55 , pp. 1211
- Berridge, M.S.¹ Franceschini, M.P.² Rosenfeld, E.³ Tewson, T.J.⁴

41
- 33845551168
- (a) Berridge, M. S.; Franceschini, M. P.; Rosenfeld, E.; Tewson, T. J. J. Org. Chem. 1990, 55, 1211. (b) Tewson, T. J. J. Org. Chem. 1983, 48, 3507. (c) Tewson, T. J.; Soderlind, M. J. Carbohydr. Chem. 1985, 4, 529. (d) Lowe, G.; Salamone, S. J. J. Chem. Soc., Chem. Commun. 1983, 1392. (e) Chai, C. L. L.; Hepburn, T. W.; Lowe, G. J. Chem. Soc., Chem. Commun. 1991, 1403. (f) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538. (g) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
- (1983) J. Org. Chem. , vol.48 , pp. 3507
- Tewson, T.J.¹

42
- 0000443147
- (a) Berridge, M. S.; Franceschini, M. P.; Rosenfeld, E.; Tewson, T. J. J. Org. Chem. 1990, 55, 1211. (b) Tewson, T. J. J. Org. Chem. 1983, 48, 3507. (c) Tewson, T. J.; Soderlind, M. J. Carbohydr. Chem. 1985, 4, 529. (d) Lowe, G.; Salamone, S. J. J. Chem. Soc., Chem. Commun. 1983, 1392. (e) Chai, C. L. L.; Hepburn, T. W.; Lowe, G. J. Chem. Soc., Chem. Commun. 1991, 1403. (f) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538. (g) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
- (1985) J. Carbohydr. Chem. , vol.4 , pp. 529
- Tewson, T.J.¹ Soderlind, M.²

43
- 37049099992
- (a) Berridge, M. S.; Franceschini, M. P.; Rosenfeld, E.; Tewson, T. J. J. Org. Chem. 1990, 55, 1211. (b) Tewson, T. J. J. Org. Chem. 1983, 48, 3507. (c) Tewson, T. J.; Soderlind, M. J. Carbohydr. Chem. 1985, 4, 529. (d) Lowe, G.; Salamone, S. J. J. Chem. Soc., Chem. Commun. 1983, 1392. (e) Chai, C. L. L.; Hepburn, T. W.; Lowe, G. J. Chem. Soc., Chem. Commun. 1991, 1403. (f) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538. (g) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
- (1983) J. Chem. Soc., Chem. Commun. , pp. 1392
- Lowe, G.¹ Salamone, S.J.²

44
- 0025886872
- (a) Berridge, M. S.; Franceschini, M. P.; Rosenfeld, E.; Tewson, T. J. J. Org. Chem. 1990, 55, 1211. (b) Tewson, T. J. J. Org. Chem. 1983, 48, 3507. (c) Tewson, T. J.; Soderlind, M. J. Carbohydr. Chem. 1985, 4, 529. (d) Lowe, G.; Salamone, S. J. J. Chem. Soc., Chem. Commun. 1983, 1392. (e) Chai, C. L. L.; Hepburn, T. W.; Lowe, G. J. Chem. Soc., Chem. Commun. 1991, 1403. (f) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538. (g) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
- (1991) J. Chem. Soc., Chem. Commun. , pp. 1403
- Chai, C.L.L.¹ Hepburn, T.W.² Lowe, G.³

45
- 9644292316
- (a) Berridge, M. S.; Franceschini, M. P.; Rosenfeld, E.; Tewson, T. J. J. Org. Chem. 1990, 55, 1211. (b) Tewson, T. J. J. Org. Chem. 1983, 48, 3507. (c) Tewson, T. J.; Soderlind, M. J. Carbohydr. Chem. 1985, 4, 529. (d) Lowe, G.; Salamone, S. J. J. Chem. Soc., Chem. Commun. 1983, 1392. (e) Chai, C. L. L.; Hepburn, T. W.; Lowe, G. J. Chem. Soc., Chem. Commun. 1991, 1403. (f) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538. (g) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 7538
- Gao, Y.¹ Sharpless, K.B.²

46
- 0000856304
- (a) Berridge, M. S.; Franceschini, M. P.; Rosenfeld, E.; Tewson, T. J. J. Org. Chem. 1990, 55, 1211. (b) Tewson, T. J. J. Org. Chem. 1983, 48, 3507. (c) Tewson, T. J.; Soderlind, M. J. Carbohydr. Chem. 1985, 4, 529. (d) Lowe, G.; Salamone, S. J. J. Chem. Soc., Chem. Commun. 1983, 1392. (e) Chai, C. L. L.; Hepburn, T. W.; Lowe, G. J. Chem. Soc., Chem. Commun. 1991, 1403. (f) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538. (g) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
- (1989) Tetrahedron Lett. , vol.30 , pp. 655
- Kim, B.M.¹ Sharpless, K.B.²

47
- 0029126431
- 2 has been reported recently for preparation of alkenes in the sugar series: Chao, B.; McNulty, K. C.; Dittmer, D. C. Tetrahedron Lett. 1995, 36, 7209.
- (1995) Tetrahedron Lett. , vol.36 , pp. 7209
- Chao, B.¹ McNulty, K.C.² Dittmer, D.C.³

48
- 0025808638
- and references therein
- Cf. Gao, Y.; Zepp, C. M. Tetrahedron Lett. 1991, 32, 3155 and references therein.
- (1991) Tetrahedron Lett. , vol.32 , pp. 3155
- Gao, Y.¹ Zepp, C.M.²

49
- 0007744494
- Cf. Carlsen, P. H. J.; Aase, K. Acta Chem. Scand. 1993, 47, 617.
- (1993) Acta Chem. Scand. , vol.47 , pp. 617
- Carlsen, P.H.J.¹ Aase, K.²

50
- 0002231746
- (a) Carnahan, J. C., Jr.; Closson, W. D. Tetrahedron Lett. 1972, 3447.
- (1972) Tetrahedron Lett. , pp. 3447
- Carnahan Jr., J.C.¹ Closson, W.D.²

51
- 0026782695
- (b) Cf. Guijarro, D.; Mancheño, B.; Yus, M. Tetrahedron Lett. 1992, 33, 5597.
- (1992) Tetrahedron Lett. , vol.33 , pp. 5597
- Guijarro, D.¹ Mancheño, B.² Yus, M.³

52
- 3643081597
- E.g. (a) Bladon, P.; Owen, L. N. J. Chem. Soc. 1950, 598. (b) Wendler, N. L.; Slates, H. L.; Tischler, M. J. Am. Chem. Soc. 1952, 74, 4894. (c) Köll, P.; Kopf, J.; Metzger, J. O.; Schwarting, W.; Oelting, M. Liebigs Ann. Chem. 1987, 199. (d) Baptistella, L. H. B.; Neto, A. Z.; Onaga, H.; Godoi, E. A. M. Tetrahedron Lett. 1993, 34, 8407. (e) Anzai, K.; Matsui, M. Agric. Biol. Chem. 1973, 37, 345. (f) Yadav, J. S.; Sreenivasa Rao, E.; Sreenivasa Rao, V. Synth. Commun. 1989, 19, 705. (g) Cf. Cleophax, J.; Hildesheim, J.; Gero, S. D. Bull. Soc. Chim. Fr. 1967, 4111.
- (1950) J. Chem. Soc. , vol.598
- Bladon, P.¹ Owen, L.N.²

53
- 3643101312
- E.g. (a) Bladon, P.; Owen, L. N. J. Chem. Soc. 1950, 598. (b) Wendler, N. L.; Slates, H. L.; Tischler, M. J. Am. Chem. Soc. 1952, 74, 4894. (c) Köll, P.; Kopf, J.; Metzger, J. O.; Schwarting, W.; Oelting, M. Liebigs Ann. Chem. 1987, 199. (d) Baptistella, L. H. B.; Neto, A. Z.; Onaga, H.; Godoi, E. A. M. Tetrahedron Lett. 1993, 34, 8407. (e) Anzai, K.; Matsui, M. Agric. Biol. Chem. 1973, 37, 345. (f) Yadav, J. S.; Sreenivasa Rao, E.; Sreenivasa Rao, V. Synth. Commun. 1989, 19, 705. (g) Cf. Cleophax, J.; Hildesheim, J.; Gero, S. D. Bull. Soc. Chim. Fr. 1967, 4111.
- (1952) J. Am. Chem. Soc. , vol.74 , pp. 4894
- Wendler, N.L.¹ Slates, H.L.² Tischler, M.³

54
- 84985240010
- E.g. (a) Bladon, P.; Owen, L. N. J. Chem. Soc. 1950, 598. (b) Wendler, N. L.; Slates, H. L.; Tischler, M. J. Am. Chem. Soc. 1952, 74, 4894. (c) Köll, P.; Kopf, J.; Metzger, J. O.; Schwarting, W.; Oelting, M. Liebigs Ann. Chem. 1987, 199. (d) Baptistella, L. H. B.; Neto, A. Z.; Onaga, H.; Godoi, E. A. M. Tetrahedron Lett. 1993, 34, 8407. (e) Anzai, K.; Matsui, M. Agric. Biol. Chem. 1973, 37, 345. (f) Yadav, J. S.; Sreenivasa Rao, E.; Sreenivasa Rao, V. Synth. Commun. 1989, 19, 705. (g) Cf. Cleophax, J.; Hildesheim, J.; Gero, S. D. Bull. Soc. Chim. Fr. 1967, 4111.
- (1987) Liebigs Ann. Chem. , pp. 199
- Köll, P.¹ Kopf, J.² Metzger, J.O.³ Schwarting, W.⁴ Oelting, M.⁵

55
- 0027730905
- E.g. (a) Bladon, P.; Owen, L. N. J. Chem. Soc. 1950, 598. (b) Wendler, N. L.; Slates, H. L.; Tischler, M. J. Am. Chem. Soc. 1952, 74, 4894. (c) Köll, P.; Kopf, J.; Metzger, J. O.; Schwarting, W.; Oelting, M. Liebigs Ann. Chem. 1987, 199. (d) Baptistella, L. H. B.; Neto, A. Z.; Onaga, H.; Godoi, E. A. M. Tetrahedron Lett. 1993, 34, 8407. (e) Anzai, K.; Matsui, M. Agric. Biol. Chem. 1973, 37, 345. (f) Yadav, J. S.; Sreenivasa Rao, E.; Sreenivasa Rao, V. Synth. Commun. 1989, 19, 705. (g) Cf. Cleophax, J.; Hildesheim, J.; Gero, S. D. Bull. Soc. Chim. Fr. 1967, 4111.
- (1993) Tetrahedron Lett. , vol.34 , pp. 8407
- Baptistella, L.H.B.¹ Neto, A.Z.² Onaga, H.³ Godoi, E.A.M.⁴

56
- 0015800963
- E.g. (a) Bladon, P.; Owen, L. N. J. Chem. Soc. 1950, 598. (b) Wendler, N. L.; Slates, H. L.; Tischler, M. J. Am. Chem. Soc. 1952, 74, 4894. (c) Köll, P.; Kopf, J.; Metzger, J. O.; Schwarting, W.; Oelting, M. Liebigs Ann. Chem. 1987, 199. (d) Baptistella, L. H. B.; Neto, A. Z.; Onaga, H.; Godoi, E. A. M. Tetrahedron Lett. 1993, 34, 8407. (e) Anzai, K.; Matsui, M. Agric. Biol. Chem. 1973, 37, 345. (f) Yadav, J. S.; Sreenivasa Rao, E.; Sreenivasa Rao, V. Synth. Commun. 1989, 19, 705. (g) Cf. Cleophax, J.; Hildesheim, J.; Gero, S. D. Bull. Soc. Chim. Fr. 1967, 4111.
- (1973) Agric. Biol. Chem. , vol.37 , pp. 345
- Anzai, K.¹ Matsui, M.²

57
- 84949694306
- E.g. (a) Bladon, P.; Owen, L. N. J. Chem. Soc. 1950, 598. (b) Wendler, N. L.; Slates, H. L.; Tischler, M. J. Am. Chem. Soc. 1952, 74, 4894. (c) Köll, P.; Kopf, J.; Metzger, J. O.; Schwarting, W.; Oelting, M. Liebigs Ann. Chem. 1987, 199. (d) Baptistella, L. H. B.; Neto, A. Z.; Onaga, H.; Godoi, E. A. M. Tetrahedron Lett. 1993, 34, 8407. (e) Anzai, K.; Matsui, M. Agric. Biol. Chem. 1973, 37, 345. (f) Yadav, J. S.; Sreenivasa Rao, E.; Sreenivasa Rao, V. Synth. Commun. 1989, 19, 705. (g) Cf. Cleophax, J.; Hildesheim, J.; Gero, S. D. Bull. Soc. Chim. Fr. 1967, 4111.
- (1989) Synth. Commun. , vol.19 , pp. 705
- Yadav, J.S.¹ Sreenivasa Rao, E.² Sreenivasa Rao, V.³

58
- 3643129422
- E.g. (a) Bladon, P.; Owen, L. N. J. Chem. Soc. 1950, 598. (b) Wendler, N. L.; Slates, H. L.; Tischler, M. J. Am. Chem. Soc. 1952, 74, 4894. (c) Köll, P.; Kopf, J.; Metzger, J. O.; Schwarting, W.; Oelting, M. Liebigs Ann. Chem. 1987, 199. (d) Baptistella, L. H. B.; Neto, A. Z.; Onaga, H.; Godoi, E. A. M. Tetrahedron Lett. 1993, 34, 8407. (e) Anzai, K.; Matsui, M. Agric. Biol. Chem. 1973, 37, 345. (f) Yadav, J. S.; Sreenivasa Rao, E.; Sreenivasa Rao, V. Synth. Commun. 1989, 19, 705. (g) Cf. Cleophax, J.; Hildesheim, J.; Gero, S. D. Bull. Soc. Chim. Fr. 1967, 4111.
- (1967) Bull. Soc. Chim. Fr. , pp. 4111
- Cleophax, J.¹ Hildesheim, J.² Gero, S.D.³

59
- 0001027768
- and references therein
- Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641, and references therein.
- (1982) J. Org. Chem. , vol.47 , pp. 1641
- Clive, D.L.J.¹ Anderson, P.C.² Moss, N.³ Singh, A.⁴

60
- 0001042103
- Björgvinsson, M.; Schrobilgen, G. J. Inorg. Chem. 1991, 30, 2540.
- (1991) J. Inorg. Chem. , vol.30 , pp. 2540
- Björgvinsson, M.¹ Schrobilgen, G.²

61
- 0006128528
- Barton, D. H. R.; Fekih, A.; Lusinchi, X. Tetrahedron Lett. 1985, 26, 6197.
- (1985) Tetrahedron Lett. , vol.26 , pp. 6197
- Barton, D.H.R.¹ Fekih, A.² Lusinchi, X.³

62
- 0007660127
- (a) Higa, K. T.; Harris, D. C. Organometallics 1989, 8, 1674.
- (1989) Organometallics , vol.8 , pp. 1674
- Higa, K.T.¹ Harris, D.C.²

63
- 0005890326
- (b) Junk, T.; Gritzner, G.; Irgolic, K. J. Synth. React. Inorg. Met.-Org. Chem. 1989, 19, 931.
- (1989) J. Synth. React. Inorg. Met.-Org. Chem. , vol.19 , pp. 931
- Junk, T.¹ Gritzner, G.² Irgolic, K.³

64
- 84980120525
- (c) Tschugaeff, L.; Choplin, W. Chem. Ber. 1914, 47, 1269.
- (1914) Chem. Ber. , vol.47 , pp. 1269
- Tschugaeff, L.¹ Choplin, W.²

65
- 33847089741
- (d) Spencer, H. K.; Cava, M. P. J. Org. Chem. 1977, 42, 2937.
- (1977) J. Org. Chem. , vol.42 , pp. 2937
- Spencer, H.K.¹ Cava, M.P.²

66
- 3643072127
- (e) Lue, P.; Chen, B.; Yu, X.; Chen, J.; Zhou, X. Synth. Commun. 1986, 16, 1849.
- (1986) J.; Zhou, X. Synth. Commun. , vol.16 , pp. 1849
- Lue, P.¹ Chen, B.² Yu, X.³ Chen⁴

67
- 0141790641
- (f) Cf. Bergman, J.; Engman, L. Z. Naturforsch. B 1980, 35, 217.
- (1980) Z. Naturforsch. B , vol.35 , pp. 217
- Bergman, J.¹ Engman, L.²

68
- 0000058795
- (g) Cf. Lalancette, J. M.; Arnac, M. Can. J. Chem. 1969, 47, 3695.
- (1969) Can. J. Chem. , vol.47 , pp. 3695
- Lalancette, J.M.¹ Arnac, M.²

69
- 85082940511
- (h) Chen, J.; Zhou, X. J. Synthesis 1987, 586.
- (1987) Synthesis , pp. 586
- Chen, J.¹ Zhou, X.J.²

70
- 0343781741
- (i) Suzuki, H.; Inouye, M. Chem. Lett. 1986, 403.
- (1986) Chem. Lett. , pp. 403
- Suzuki, H.¹ Inouye, M.²

71
- 0040897142
- (j) Suzuki, H.; Manabe, H.; Kawaguchi, T.; Inouye, M. Bull. Chem. Soc. Jpn. 1987, 60, 771.
- (1987) Bull. Chem. Soc. Jpn. , vol.60 , pp. 771
- Suzuki, H.¹ Manabe, H.² Kawaguchi, T.³ Inouye, M.⁴

72
- 0027388965
- (k) Suzuki, H.; Nakamura, T. J. Org. Chem. 1993, 58, 241.
- (1993) J. Org. Chem. , vol.58 , pp. 241
- Suzuki, H.¹ Nakamura, T.²

73
- 33845379130
- Gautheron, B.; Tainturier, G.; Degrand, C. J. Am. Chem. Soc. 1985, 107, 5579. Cf. Degrand, C.; Prest, R. J. Electroanal. Chem. 1990, 282, 281.
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 5579
- Gautheron, B.¹ Tainturier, G.² Degrand, C.³

74
- 0000980481
- Gautheron, B.; Tainturier, G.; Degrand, C. J. Am. Chem. Soc. 1985, 107, 5579. Cf. Degrand, C.; Prest, R. J. Electroanal. Chem. 1990, 282, 281.
- (1990) J. Electroanal. Chem. , vol.282 , pp. 281
- Degrand, C.¹ Prest, R.²

75
- 33751574570
- Cf. Rossi, R. A.; Peñéñory, A. B. J. Org. Chem. 1981, 46, 4580.
- (1981) J. Org. Chem. , vol.46 , pp. 4580
- Rossi, R.A.¹ Peñéñory, A.B.²

76
- 0000038588
- Gladysz, J. A.; Hornby, J. L.; Garbe, J. E. J. Org. Chem. 1978, 43, 1204.
- (1978) J. Org. Chem. , vol.43 , pp. 1204
- Gladysz, J.A.¹ Hornby, J.L.² Garbe, J.E.³

77
- 0000698622
- Gladysz, J. A.; Wong, V. K.; Jick, B. S. Tetrahedron 1979, 35, 2329.
- (1979) Tetrahedron , vol.35 , pp. 2329
- Gladysz, J.A.¹ Wong, V.K.² Jick, B.S.³

78
- 0141991523
- Durst, T.; Tin, K.-C. Can. J. Chem. 1970, 48, 845.
- (1970) J. Chem. , vol.48 , pp. 845
- Durst, T.¹ Can, T.K.-C.²

79
- 3643062760
- note
- 12C) the molecule is unsymmetrical and the coupling can be measured.

80
- 0025869521
- (a) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161.
- (1991) J. Org. Chem. , vol.56 , pp. 2161
- Cosford, N.D.P.¹ Schinazi, R.F.²

81
- 0027415213
- (b) Cosford, N. D. P.; Schinazi, F. Nucleosides Nucleotides 1993, 12, 149.
- (1993) Nucleosides Nucleotides , vol.12 , pp. 149
- Cosford, N.D.P.¹ Schinazi, F.²

82
- 0024948979
- E.g. (a) Kaskar, B.; Markovac, A. J. Heterocycl. Chem. 1989, 26, 1531. Removal of 5′-O-trityl and acyl groups from 3′-deoxythymidine: (b) Sekine, M.; Nakanishi, T. J. Org. Chem. 1990, 55, 924.
- (1989) J. Heterocycl. Chem. , vol.26 , pp. 1531
- Kaskar, B.¹ Markovac, A.²

83
- 0025356805
- E.g. (a) Kaskar, B.; Markovac, A. J. Heterocycl. Chem. 1989, 26, 1531. Removal of 5′-O-trityl and acyl groups from 3′-deoxythymidine: (b) Sekine, M.; Nakanishi, T. J. Org. Chem. 1990, 55, 924.
- (1990) J. Org. Chem. , vol.55 , pp. 924
- Sekine, M.¹ Nakanishi, T.²

84
- 0026632988
- Manchand, P. S.; Belica, P. S.; Holman, M. J.; Huang, T.-N.; Maehr, H.; Tam, S. Y.-K.; Yang, R. T. J. Org. Chem. 1992, 57, 3473.
- (1992) J. Org. Chem. , vol.57 , pp. 3473
- Manchand, P.S.¹ Belica, P.S.² Holman, M.J.³ Huang, T.-N.⁴ Maehr, H.⁵ Tam, S.Y.-K.⁶ Yang, R.T.⁷

85
- 3643115980
- Supplied by Chemical Dynamics Corp., South Plainfield, NJ
- Supplied by Chemical Dynamics Corp., South Plainfield, NJ.

86
- 85088619811
- note
- 4 (15 mL).

87
- 85088620301
- note
- 4 (6 mL) and EtOH (94 mL).

88
- 3643071076
- Ferdinand Enke: Stuttgart
- Cf. Brauer, G., Ed. Handbuch der Präparativen Anorganischen Chemie; Ferdinand Enke: Stuttgart, 1975; Vol. I, p 431.
- (1975) Handbuch der Präparativen Anorganischen Chemie , vol.1 , pp. 431
- Brauer, G.¹

89
- 0005873219
- Lambert, J. B.; Fabricius, D. M.; Hoard, J. A. J. Org. Chem. 1979, 44, 1480. In preparing the butenylnaphthalene, we used allyl-lithium, generated (Seyferth, D.; Weiner, M. A.; J. Org. Chem. 1961, 26, 4797) from triphenyl(2-propenyl)stannane.
- (1979) J. Org. Chem. , vol.44 , pp. 1480
- Lambert, J.B.¹ Fabricius, D.M.² Hoard, J.A.³

90
- 16144365031
- Lambert, J. B.; Fabricius, D. M.; Hoard, J. A. J. Org. Chem. 1979, 44, 1480. In preparing the butenylnaphthalene, we used allyl-lithium, generated (Seyferth, D.; Weiner, M. A.; J. Org. Chem. 1961, 26, 4797) from triphenyl(2-propenyl)stannane.
- (1961) J. Org. Chem. , vol.26 , pp. 4797
- Seyferth, D.¹ Weiner, M.A.²

91
- 3643100295
- Shonle, H. A.; Row, P. Q. J. Am. Chem. Soc. 1921, 43, 361.
- (1921) J. Am. Chem. Soc. , vol.43 , pp. 361
- Shonle, H.A.¹ Row, P.Q.²

92
- 0040310217
- Using literature procedures, methyl 2,3-O-isopropylidene-β-D-ribofuranoside (Levene, P. A.; Stiller, E. T. J. Biol. Chem. 1934, 104, 299. Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1980, 55, 3853) was converted into its 5-O-benzyl derivative (Tener, G. M.; Khorana, H. G. J. Am. Chem. Soc. 1957, 79, 437) and then into methyl 5-O-benzyl-β-D-ribofuranoside (Kawana, M.; Kuzuhara, H.; Emoto, S. Bull. Chem. Soc. Jpn. 1981, 54, 1492).
- (1934) J. Biol. Chem. , vol.104 , pp. 299
- Levene, P.A.¹ Stiller, E.T.²

93
- 0025041272
- Using literature procedures, methyl 2,3-O-isopropylidene-β-D-ribofuranoside (Levene, P. A.; Stiller, E. T. J. Biol. Chem. 1934, 104, 299. Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1980, 55, 3853) was converted into its 5-O-benzyl derivative (Tener, G. M.; Khorana, H. G. J. Am. Chem. Soc. 1957, 79, 437) and then into methyl 5-O-benzyl-β-D-ribofuranoside (Kawana, M.; Kuzuhara, H.; Emoto, S. Bull. Chem. Soc. Jpn. 1981, 54, 1492).
- (1980) J. Org. Chem. , vol.55 , pp. 3853
- Barrett, A.G.M.¹ Lebold, S.A.²

94
- 7044277214
- Using literature procedures, methyl 2,3-O-isopropylidene-β-D-ribofuranoside (Levene, P. A.; Stiller, E. T. J. Biol. Chem. 1934, 104, 299. Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1980, 55, 3853) was converted into its 5-O-benzyl derivative (Tener, G. M.; Khorana, H. G. J. Am. Chem. Soc. 1957, 79, 437) and then into methyl 5-O-benzyl-β-D-ribofuranoside (Kawana, M.; Kuzuhara, H.; Emoto, S. Bull. Chem. Soc. Jpn. 1981, 54, 1492).
- (1957) J. Am. Chem. Soc. , vol.79 , pp. 437
- Tener, G.M.¹ Khorana, H.G.²

95
- 0001084227
- Using literature procedures, methyl 2,3-O-isopropylidene-β-D-ribofuranoside (Levene, P. A.; Stiller, E. T. J. Biol. Chem. 1934, 104, 299. Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1980, 55, 3853) was converted into its 5-O-benzyl derivative (Tener, G. M.; Khorana, H. G. J. Am. Chem. Soc. 1957, 79, 437) and then into methyl 5-O-benzyl-β-D-ribofuranoside (Kawana, M.; Kuzuhara, H.; Emoto, S. Bull. Chem. Soc. Jpn. 1981, 54, 1492).
- (1981) Bull. Chem. Soc. Jpn. , vol.54 , pp. 1492
- Kawana, M.¹ Kuzuhara, H.² Emoto, S.³

96
- 0000523862
- Taniguchi, M.; Koga, K.; Yamada, S. Tetrahedron 1974, 30, 3547.
- (1974) Tetrahedron , vol.30 , pp. 3547
- Taniguchi, M.¹ Koga, K.² Yamada, S.³

97
- 0005220594
- (a) Codington, J. F.; Doehr, I. L.; Fox, J. J. J. Org. Chem. 1964, 29, 558.
- (1964) J. Org. Chem. , vol.29 , pp. 558
- Codington, J.F.¹ Doehr, I.L.² Fox, J.J.³

98
- 0004409513
- Wiley: New York
- (b) Synthetic Procedures in Nucleic Acid Chemistry; Zorbach, W. W., Tipson, R. S. Ed.; Wiley: New York, 1968; Vol. 1, p 441.
- (1968) Synthetic Procedures in Nucleic Acid Chemistry , vol.1 , pp. 441
- Zorbach, W.W.¹ Tipson, R.S.²

99
- 0027090091
- Cf. Johnson, R.; Joshi, B. V.; Neidle, S.; Reese, C. B.; Snook, C. F. Tetrahedron Lett. 1992, 33, 8151.
- (1992) Tetrahedron Lett. , vol.33 , pp. 8151
- Johnson, R.¹ Joshi, B.V.² Neidle, S.³ Reese, C.B.⁴ Snook, C.F.⁵

100
- 0025738008
- Huang, J.-T.; Chen, L.-C.; Wang, L.; Kim, M.-H.; Warshaw, J. A.; Armstrong, D.; Zhu, Q.-Y.; Chou, T.-C.; Watanabe, K. A.; Matulic-Adamic, J.; Su, T-L.; Fox, J. J.; Polsky, B.; Baron, P. A.; Gold, J. W. M.; Hardy, W. D.; Zuckerman, E. J. Med. Chem. 1991, 34, 1640.
- (1991) J. Med. Chem. , vol.34 , pp. 1640
- Huang, J.-T.¹ Chen, L.-C.² Wang, L.³ Kim, M.-H.⁴ Warshaw, J.A.⁵ Armstrong, D.⁶ Zhu, Q.-Y.⁷ Chou, T.-C.⁸ Watanabe, K.A.⁹ Matulic-Adamic, J.¹⁰ Su, T.-L.¹¹ Fox, J.J.¹² Polsky, B.¹³ Baron, P.A.¹⁴ Gold, J.W.M.¹⁵ Hardy, W.D.¹⁶ Zuckerman, E.¹⁷

101
- 0010446130
- 2O) 482.1842, found 482.1843.
- (1957) J. Am. Chem. Soc. , vol.79 , pp. 2775
- Fox, J.J.¹ Yung, N.² Bendich, A.³

102
- 0014912181
- Blank, H.-U.; Pfleiderer, W. Justus Liebigs Ann. Chem. 1970, 742, 16.
- (1970) Justus Liebigs Ann. Chem. , vol.742 , pp. 16
- Blank, H.-U.¹ Pfleiderer, W.²

103
- 0011250653
- Watanabe, K. A.; Fox, J. J. Angew. Chem. 1966, 78, 589.
- (1966) J. Angew. Chem. , vol.78 , pp. 589
- Watanabe, K.A.¹ Fox, J.²

104
- 0014086399
- Fromageot, H. P. M.; Griffin, B. E.; Reese, C. B.; Sulston, J. E. Tetrahedron 1967, 23, 2315.
- (1967) Tetrahedron , vol.23 , pp. 2315
- Fromageot, H.P.M.¹ Griffin, B.E.² Reese, C.B.³ Sulston, J.E.⁴

105
- 3643053253
- note
- 6, 200 MHz) δ 2.08 (s, 3 H), 4.10-4.38 (m, 5 H), 4.38-4.58 (br s, 1 H), 4.60-4.85 (br s, 1 H), 5.60-5.70 (d, J = 8.0 Hz, 1 H), 5.82-5.92 (d, J = 4.0 Hz, 1 H), 7.62-7.72 (d, J = 8.0 Hz, 1 H), 9.75-10.25 (br s, 1 H).

106
- 0025811726
- Amino, Y.; Iwagami, H. Chem. Pharm. Bull. 1991, 39, 622.
- (1991) Chem. Pharm. Bull. , vol.39 , pp. 622
- Amino, Y.¹ Iwagami, H.²

107
- 3643061711
- PCT Int. Appl. WO 93 12, 128, 24 Jun 1993
- We thank Dr. G. A. Angoh (Raylo Chemicals) for a gift of this compound. Cf. Imbach, J. L.; Gosselin, G. PCT Int. Appl. WO 93 12, 128, 24 Jun 1993; Chem. Abstr. 1994, 120, 135074u.
- (1994) Chem. Abstr. , vol.120
- Imbach, J.L.¹ Gosselin, G.²

108
- 0040155755
- RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 986
- Rajanbabu, T.V.¹ Nugent, W.A.²

109
- 0026605676
- Vinayak, R.; Anderson, P.; McCollum, C.; Hampel, A. Nucleic Acids Res. 1992, 20, 1265.
- (1992) Nucleic Acids Res. , vol.20 , pp. 1265
- Vinayak, R.¹ Anderson, P.² McCollum, C.³ Hampel, A.⁴

110
- 3643097134
- JP 05 65,285, 19 Mar 1993
- Kajiwara, A. JP 05 65,285, 19 Mar 1993; Chem. Abstr. 1993, 119, 226352d.
- (1993) Chem. Abstr. , vol.119
- Kajiwara, A.¹

111
- 3643111752
- Shasha, B. S.; Doane, W. M. Carbohydr. Res. 1974, 34, 370.
- (1974) Carbohydr. Res. , vol.34 , pp. 370
- Shasha, B.S.¹ Doane, W.M.²

112
- 0013435164
- Josan, J. S.; Eastwood, F. W. Carbohydr. Res. 1968, 7, 161.
- (1968) Carbohydr. Res. , vol.7 , pp. 161
- Josan, J.S.¹ Eastwood, F.W.²

113
- 0041533873
- Prepared (88% yield) by the reported method (Kuszmann, J.; Sohár, P. Carbohydr. Res, 1979, 74, 187). The parent diol was prepared (36% yield) according to: Chittenden, G. J. F. Carbohydr. Res. 1982, 108, 81.
- (1979) Carbohydr. Res , vol.74 , pp. 187
- Kuszmann, J.¹ Sohár, P.²

114
- 0003433730
- Prepared (88% yield) by the reported method (Kuszmann, J.; Sohár, P. Carbohydr. Res, 1979, 74, 187). The parent diol was prepared (36% yield) according to: Chittenden, G. J. F. Carbohydr. Res. 1982, 108, 81.
- (1982) Carbohydr. Res. , vol.108 , pp. 81
- Chittenden, G.J.F.¹

115
- 84918614343
- Kuszmann, J.; Sohár, P. Carbohydr. Res. 1980, 83, 63.
- (1980) Carbohydr. Res. , vol.83 , pp. 63
- Kuszmann, J.¹ Sohár, P.²

116
- 3643112836
- Takeshita, T.; Kitajima, M. Bull. Chem. Soc. Jpn. 1959, 32, 985.
- (1959) Bull. Chem. Soc. Jpn. , vol.32 , pp. 985
- Takeshita, T.¹ Kitajima, M.²

117
- 84970604266
- Patroni, J. J.; Stick, R. V.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1988, 41, 91.
- (1988) Aust. J. Chem. , vol.41 , pp. 91
- Patroni, J.J.¹ Stick, R.V.² Skelton, B.W.³ White, A.H.⁴

118
- 0038614192
- Padwa, A.; Rieker, W. F.; Rosenthal, R. J. J. Org. Chem. 1984, 49, 1353.
- (1984) J. Org. Chem. , vol.49 , pp. 1353
- Padwa, A.¹ Rieker, W.F.² Rosenthal, R.J.³

119
- 0026060841
- (a) Devine, P. N.; Oh, T. Tetrahedron Lett. 1991, 32, 883. Feit, P. W. J. Med. Chem. 1964, 7, 14.
- (1991) Tetrahedron Lett. , vol.32 , pp. 883
- Devine, P.N.¹ Oh, T.²

120
- 0002096855
- (a) Devine, P. N.; Oh, T. Tetrahedron Lett. 1991, 32, 883. Feit, P. W. J. Med. Chem. 1964, 7, 14.
- (1964) J. Med. Chem. , vol.7 , pp. 14
- Feit, P.W.¹

121
- 0002818786
- (b) Mash, E. A.; Nelson, K. A.; Van Deusen, S.; Hemperly, S. B. Org. Synth. 1988, 68, 92.
- (1988) Org. Synth. , vol.68 , pp. 92
- Mash, E.A.¹ Nelson, K.A.² Van Deusen, S.³ Hemperly, S.B.⁴

122
- 0000978196
- (a) Benn, R.; Jolly, P. W.; Mynott, R.; Schenker, G. Organometallics 1985, 4, 1136.
- (1985) Organometallics , vol.4 , pp. 1136
- Benn, R.¹ Jolly, P.W.² Mynott, R.³ Schenker, G.⁴

123
- 0001254524
- (b) Kawai, T.; Yamazaki, Y.; Taoka, T.; Kobayashi, K. J. Catal. 1984, 89, 452.
- (1984) J. Catal. , vol.89 , pp. 452
- Kawai, T.¹ Yamazaki, Y.² Taoka, T.³ Kobayashi, K.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.