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Volumn , Issue 23, 2006, Pages 5279-5292

Regiospecific synthesis of 4-deoxy-D-threo-hex-3-enopyranosides by simultaneous activation-elimination of the talopyranoside axial 4-OH with the NaH/Im2SO2 system: Manifestation of the stereoelectronic effect

(3) Attolino, Emanuele a Catelani, Giorgio a D'Andrea, Felicia a

a UNIVERSITY OF PISA (Italy)

Author keywords

Carbohydrates; Elimination; Hex 3 enopyranosides; Imidazylates; Stereoelectronic effect; Talopyranosides

Indexed keywords

EID: 33845458080 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.200600526 Document Type: Article

Times cited : (14)

References (58)

1
- 0001655270
- (Eds.: W. Pigman, D. Horton), Academic Press, San Diego
- R. J. Ferrier, The Carbohydrates, Chemistry and Biochemistry (Eds.: W. Pigman, D. Horton), Academic Press, San Diego, 1980, vol. 1B, pp. 843-879.
- (1980) The Carbohydrates, Chemistry and Biochemistry , vol.1 B , pp. 843-879
- Ferrier, R.J.¹

2
- 0004138595
- John Wiley & Sons, Chichester
- P.Collins, R. Ferrier, Monosaccharides: their chemistry and their roles in natural products, John Wiley & Sons, Chichester, 1995, pp. 217-265.
- (1995) Monosaccharides: Their Chemistry and Their Roles in Natural Products , pp. 217-265
- Collins, P.¹ Ferrier, R.²

3
- 33645773127
- and references cited therein
- H. Dong, Z. Pei, O. Ramström, J. Org. Chem. 2006, 71, 3306-3309 and references cited therein.
- (2006) J. Org. Chem. , vol.71 , pp. 3306-3309
- Dong, H.¹ Pei, Z.² Ramström, O.³

4
- 0342887285
- a) T. Tsuchiya, F. Nakamura, S. Umezawa, Tetrahedron Lett. 1979, 20, 2805-2808;
- (1979) Tetrahedron Lett. , vol.20 , pp. 2805-2808
- Tsuchiya, T.¹ Nakamura, F.² Umezawa, S.³

5
- 0020045492
- b) J. D. Prugh, A. A. Deana, Tetrahedron Lett. 1982, 23, 281-284;
- (1982) Tetrahedron Lett. , vol.23 , pp. 281-284
- Prugh, J.D.¹ Deana, A.A.²

6
- 0000641940
- c) E. P. Barrette, L. Goodman, J. Org. Chem. 1984, 49, 176-178.
- (1984) J. Org. Chem. , vol.49 , pp. 176-178
- Barrette, E.P.¹ Goodman, L.²

7
- 0014624453
- a) D. H. Ball, F. W. Parrish, Adv. Carbohydr. Chem. Biochem. 1969, 24, 139;
- (1969) Adv. Carbohydr. Chem. Biochem. , vol.24 , pp. 139
- Ball, D.H.¹ Parrish, F.W.²

8
- 33845445410
- b) D. H. Ball, F. W. Parrish, Adv. Carbohydr. Chem. Biochem. 1968, 23, 223.
- (1968) Adv. Carbohydr. Chem. Biochem. , vol.23 , pp. 223
- Ball, D.H.¹ Parrish, F.W.²

9
- 84981948104
- K. Freudenberg, F. Brauns, Ber. Dtsch. Chem. Ges. 1922, 55, 3233.
- (1922) Ber. Dtsch. Chem. Ges. , vol.55 , pp. 3233
- Freudenberg, K.¹ Brauns, F.²

10
- 84862333037
- a) F. Chètrien, Synth. Commun. 1989, 19, 1015;
- (1989) Synth. Commun. , vol.19 , pp. 1015
- Chètrien, F.¹

11
- 0041739073
- b) A. Corsaro, G. Catelani, F. D'Andrea, S. Fisichella, M. Mariani, V. Pistarà, Environ. Sci. Pollut. Res. 2003, 10, 325-328;
- (2003) Environ. Sci. Pollut. Res. , vol.10 , pp. 325-328
- Corsaro, A.¹ Catelani, G.² D'Andrea, F.³ Fisichella, S.⁴ Mariani, M.⁵ Pistarà, V.⁶

12
- 0142200364
- c) G. Catelani, A. Corsaro, F. D'Andrea, M. Mariani, V. Pistarà, E. Vittorino, Carbohydr. Res. 2003, 338, 2349-2358.
- (2003) Carbohydr. Res. , vol.338 , pp. 2349-2358
- Catelani, G.¹ Corsaro, A.² D'Andrea, F.³ Mariani, M.⁴ Pistarà, V.⁵ Vittorino, E.⁶

13
- 0034918565
- K. M. Khan, S. Perveen, S. T. A. Shah, M. S. Shekhani, W. Voelter, New J. Chem. 2001, 25, 896-898.
- (2001) New J. Chem. , vol.25 , pp. 896-898
- Khan, K.M.¹ Perveen, S.² Shah, S.T.A.³ Shekhani, M.S.⁴ Voelter, W.⁵

14
- 0000716447
- D. Horton, J. P. Roski, P. Norris, J. Org. Chem. 1996, 61, 3783-3793.
- (1996) J. Org. Chem. , vol.61 , pp. 3783-3793
- Horton, D.¹ Roski, J.P.² Norris, P.³

15
- 77955382558
- R. W. Binkley, M. G. Ambrose, J. Carbohydr. Chem. 1984, 3, 1-49.
- (1984) J. Carbohydr. Chem. , vol.3 , pp. 1-49
- Binkley, R.W.¹ Ambrose, M.G.²

16
- 0030599356
- a) A. El Nemr, T. Tsuchiya, Y. Kobayashi, Carbohydr. Res. 1996, 293, 31-59;
- (1996) Carbohydr. Res. , vol.293 , pp. 31-59
- El Nemr, A.¹ Tsuchiya, T.² Kobayashi, Y.³

17
- 0030856258
- b) A. El Nemr, T. Tsuchiya, Carbohydr. Res. 1997, 303, 267-281;
- (1997) Carbohydr. Res. , vol.303 , pp. 267-281
- El Nemr, A.¹ Tsuchiya, T.²

18
- 0035969934
- c) A. El Nemr, T. Tsuchiya, Carbohydr. Res. 2001, 330, 205-214.
- (2001) Carbohydr. Res. , vol.330 , pp. 205-214
- El Nemr, A.¹ Tsuchiya, T.²

19
- 0030570916
- a) J. M. Vatèle, S. Hanessian, Tetrahedron 1996, 52, 10557-10568;
- (1996) Tetrahedron , vol.52 , pp. 10557-10568
- Vatèle, J.M.¹ Hanessian, S.²

20
- 0004288915
- M. Dekker, New York
- b) S. Hanessian, Preparative Carbohydrate Chemistry, M. Dekker, New York, 1997, pp. 127-149.
- (1997) Preparative Carbohydrate Chemistry , pp. 127-149
- Hanessian, S.¹

21
- 0032191220
- a) E. Bousquet, M. Khitri, L. Lay, F. Nicotra, L. Panza, G. Russo, Carbohydr. Res. 1998, 311, 171-181;
- (1998) Carbohydr. Res. , vol.311 , pp. 171-181
- Bousquet, E.¹ Khitri, M.² Lay, L.³ Nicotra, F.⁴ Panza, L.⁵ Russo, G.⁶

22
- 0000024143
- b) S. David, A. Malleron, C. Dini, Carbohydr. Res. 1989, 188, 193-200.
- (1989) Carbohydr. Res. , vol.188 , pp. 193-200
- David, S.¹ Malleron, A.² Dini, C.³

23
- 37049080709
- To the best of our knowledge, only a 4′-O-imidazylate lactoside affording an uncharacterised elimination product at room temperature has been reported by M. Bernabe, A. Fernandez-Mayoralas, J. Jimenez-Barbero, M. Martin-Lomas, A. Rivera, J. Chem. Soc., Perkin Trans. 2 1989, 1867-1873.
- (1989) J. Chem. Soc., Perkin Trans. 2 , pp. 1867-1873
- Bernabe, M.¹ Fernandez-Mayoralas, A.² Jimenez-Barbero, J.³ Martin-Lomas, M.⁴ Rivera, A.⁵

24
- 0037170148
- E. Attolino, G. Catelani, F. D'Andrea, Tetrahedron Lett. 2002, 43, 1685-1688.
- (2002) Tetrahedron Lett. , vol.43 , pp. 1685-1688
- Attolino, E.¹ Catelani, G.² D'Andrea, F.³

25
- 0030962741
- a) V. Moreau, J. C. Norrild, H. Driguez, Carbohydr. Res. 1997, 300, 271-277;
- (1997) Carbohydr. Res. , vol.300 , pp. 271-277
- Moreau, V.¹ Norrild, J.C.² Driguez, H.³

26
- 0008598215
- b) J. C. McAuliffe, R. V. Stick, Aust. J. Chem. 1997, 50, 203-208.
- (1997) Aust. J. Chem. , vol.50 , pp. 203-208
- McAuliffe, J.C.¹ Stick, R.V.²

27
- 0037010752
- a) E. Attolino, G. Catelani, F. D'Andrea, Tetrahedron Lett. 2002, 43, 8815-8818;
- (2002) Tetrahedron Lett. , vol.43 , pp. 8815-8818
- Attolino, E.¹ Catelani, G.² D'Andrea, F.³

28
- 28144441885
- b) E. Attolino, G. Catelani, F. D'Andrea, M. Nicolardi, J. Carbohydr. Chem. 2004, 23, 179-190.
- (2004) J. Carbohydr. Chem. , vol.23 , pp. 179-190
- Attolino, E.¹ Catelani, G.² D'Andrea, F.³ Nicolardi, M.⁴

29
- 0002593107
- for 4f, see
- for 4f, see a) P. L. Barili, G. Berti, G. Catelani, F. D'Andrea, Gazz. Chim. Ital. 1992, 122, 135-142;
- (1992) Gazz. Chim. Ital. , vol.122 , pp. 135-142
- Barili, P.L.¹ Berti, G.² Catelani, G.³ D'Andrea, F.⁴

30
- 0031052855
- for 4g, see
- for 4g, see b) P. L. Barili, G. Catelani, F. D'Andrea, F. De Rensis, P. Falcini, Carbohydr. Res. 1997, 295, 75-84;
- (1997) Carbohydr. Res. , vol.295 , pp. 75-84
- Barili, P.L.¹ Catelani, G.² D'Andrea, F.³ De Rensis, F.⁴ Falcini, P.⁵

31
- 0003789293
- for 4h, see
- for 4h, see; c) J. Schneider, Y. C. Lee, H. M. Flowers, Carbohydr. Res. 1974, 36, 159-166;
- (1974) Carbohydr. Res. , vol.36 , pp. 159-166
- Schneider, J.¹ Lee, Y.C.² Flowers, H.M.³

32
- 84970619138
- for 4i, see
- for 4i, see; d) V. Ferro, B. W. Skelton, R. V. Stick, A. H. White, Aust. J. Chem. 1993, 46, 787-803.
- (1993) Aust. J. Chem. , vol.46 , pp. 787-803
- Ferro, V.¹ Skelton, B.W.² Stick, R.V.³ White, A.H.⁴

33
- 0025159938
- For 7 and 9, see
- For 7 and 9, see P. L. Barili, G. Berti, D. Bertozzi, G. Catelani, F. Colonna, T. Corsetti, F. D'Andrea, Tetrahedron 1990, 46, 5365-5376;
- (1990) Tetrahedron , vol.46 , pp. 5365-5376
- Barili, P.L.¹ Berti, G.² Bertozzi, D.³ Catelani, G.⁴ Colonna, F.⁵ Corsetti, T.⁶ D'Andrea, F.⁷

34
- 0031052855
- [18b].
- (1997) Carbohydr. Res. , vol.295 , pp. 75-84
- Barili, P.L.¹ Catelani, G.² D'Andrea, F.³ De Rensis, F.⁴ Falcini, P.⁵

35
- 0030603081
- P. L. Barili, G. Berti, G. Catelani, F. D'Andrea, V. Di Bussolo, Carbohydr. Res. 1996, 290, 17-31.
- (1996) Carbohydr. Res. , vol.290 , pp. 17-31
- Barili, P.L.¹ Berti, G.² Catelani, G.³ D'Andrea, F.⁴ Di Bussolo, V.⁵

36
- 0027997412
- S. V. Ley, W. P. Griffith, J. Norman, S. P. Marsden, Synthesis 1994, 639-666.
- (1994) Synthesis , pp. 639-666
- Ley, S.V.¹ Griffith, W.P.² Norman, J.³ Marsden, S.P.⁴

37
- 0002602063
- R. U. Lemieux, K. James, T. L. Nagabhushan, Can. J. Chem. 1973, 51, 27-32.
- (1973) Can. J. Chem. , vol.51 , pp. 27-32
- Lemieux, R.U.¹ James, K.² Nagabhushan, T.L.³

38
- 0002254247
- a) G. J. F. Chittenden, Carbohydr. Res. 1976, 52, 23-29;
- (1976) Carbohydr. Res. , vol.52 , pp. 23-29
- Chittenden, G.J.F.¹

39
- 85004234666
- b) T. Haradahira, M. Maeda, Y. Yano, M. Kojima, Chem. Pharm. Bull. 1984, 32, 3317-3319;
- (1984) Chem. Pharm. Bull. , vol.32 , pp. 3317-3319
- Haradahira, T.¹ Maeda, M.² Yano, Y.³ Kojima, M.⁴

40
- 33748645378
- c) A. Burton, P. Wyatt, G.-J. Boons, J. Chem. Soc., Perkin Trans. 1 1997, 2375-2382.
- (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 2375-2382
- Burton, A.¹ Wyatt, P.² Boons, G.-J.³

41
- 0011404935
- N. E. Nifant'ev, S. S. Mamyan, A. S. Shaskov, N. K. Kochetkov, Bioorg. Khim. 1988, 14, 187-197.
- (1988) Bioorg. Khim. , vol.14 , pp. 187-197
- Nifant'ev, N.E.¹ Mamyan, S.S.² Shaskov, A.S.³ Kochetkov, N.K.⁴

42
- 0003100131
- for 5f, see
- for 5f, see a) H. Paulsen, T. Hasenkamp, M. Paal, Carbohydr. Res. 1985, 144, 45-55;
- (1985) Carbohydr. Res. , vol.144 , pp. 45-55
- Paulsen, H.¹ Hasenkamp, T.² Paal, M.³

43
- 0033979103
- for 5g, see
- for 5g, see; b) G. Catelani, F. D'Andrea, L. Puccioni, Carbohydr. Res. 2000, 324, 204-209;
- (2000) Carbohydr. Res. , vol.324 , pp. 204-209
- Catelani, G.¹ D'Andrea, F.² Puccioni, L.³

44
- 0028970070
- for 5h, see
- for 5h, see c) D. Saibal Kumar, N. Roy, Synth. Commun. 1995, 25, 1699-1710.
- (1995) Synth. Commun. , vol.25 , pp. 1699-1710
- Saibal Kumar, D.¹ Roy, N.²

45
- 0001600073
- N. Morishima, S. Koto, M. Oshima, A. Sugimoto, S. Zen, Bull. Chem. Soc. Jpn. 1983, 56, 2849-2850.
- (1983) Bull. Chem. Soc. Jpn. , vol.56 , pp. 2849-2850
- Morishima, N.¹ Koto, S.² Oshima, M.³ Sugimoto, A.⁴ Zen, S.⁵

46
- 0348210598
- S. David, S. Hanessian, Tetrahedron 1985, 41, 643-663.
- (1985) Tetrahedron , vol.41 , pp. 643-663
- David, S.¹ Hanessian, S.²

47
- 37049073730
- a) K. Tanemura, T. Suzuki, T. Horaguchi, J. Chem. Soc., Chem. Commun. 1992, 979-980;
- (1992) J. Chem. Soc., Chem. Commun. , pp. 979-980
- Tanemura, K.¹ Suzuki, T.² Horaguchi, T.³

48
- 0029111477
- b) J. M. Garcia Fernandez, C. Ortiz Mellet, A. M. Marin, J. Fuentes, Carbohydr. Res. 1995, 274, 263-268.
- (1995) Carbohydr. Res. , vol.274 , pp. 263-268
- Garcia Fernandez, J.M.¹ Ortiz Mellet, C.² Marin, A.M.³ Fuentes, J.⁴

49
- 33845448823
- manuscript in preparation
- E. Attolino, G. Catelani, F. D'Andrea, V. Pistarà, manuscript in preparation.
- Attolino, E.¹ Catelani, G.² D'Andrea, F.³ Pistarà, V.⁴

50
- 0000507441
- A. C. Richardson, Carbohydr. Res. 1969, 10, 395-402.
- (1969) Carbohydr. Res. , vol.10 , pp. 395-402
- Richardson, A.C.¹

51
- 0003536850
- Pergamon Press, Oxford
- For a general treatment of stereoelectronic and hyperconjugative effects, see: a) P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford, 1983;
- (1983) Stereoelectronic Effects in Organic Chemistry
- Deslongchamps, P.¹

52
- 0003996777
- Sprinter-Verlag, Berlin, Heidelberg, New York
- b) A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Sprinter-Verlag, Berlin, Heidelberg, New York, 1983.
- (1983) The Anomeric Effect and Related Stereoelectronic Effects at Oxygen
- Kirby, A.J.¹

53
- 0037181391
- I. V. Alabugin, T. A. Zeidan, J. Am. Chem. Soc. 2002, 124, 3175-3185.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 3175-3185
- Alabugin, I.V.¹ Zeidan, T.A.²

54
- 18044395353
- G. Cuevas, K. Martínez-Mayorga, M. Fernández-Alonso, J. Jiménez-Barbero, C. L. Perrin, E. Juaristi, N. López-Mora, Angew. Chem. Int. Ed. 2005, 44, 2360-2364.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 2360-2364
- Cuevas, G.¹ Martínez-Mayorga, K.² Fernández-Alonso, M.³ Jiménez-Barbero, J.⁴ Perrin, C.L.⁵ Juaristi, E.⁶ López-Mora, N.⁷

55
- 30744431655
- Y. Zhu, Q. Pan, C. Thibaudeau, S. Zhao, I. Carmichael, A. S. Serianni, J. Org. Chem. 2006, 71, 466-479.
- (2006) J. Org. Chem. , vol.71 , pp. 466-479
- Zhu, Y.¹ Pan, Q.² Thibaudeau, C.³ Zhao, S.⁴ Carmichael, I.⁵ Serianni, A.S.⁶

56
- 34547130099
- K. Bock, C. Pedersen, Adv. Carbohydr. Chem. Biochem. 1983, 41, 27-66.
- (1983) Adv. Carbohydr. Chem. Biochem. , vol.41 , pp. 27-66
- Bock, K.¹ Pedersen, C.²

57
- 0004055425
- Pergamon Press, Oxford
- D. D. Perrin, W. L. F. Armarego, D. R. Perrin, Purification of Laboratory Chemicals, 2nd ed., Pergamon Press, Oxford, 1980.
- (1980) Purification of Laboratory Chemicals, 2nd Ed.
- Perrin, D.D.¹ Armarego, W.L.F.² Perrin, D.R.³

58
- 0030945697
- P. L. Barili, G. Berti, G. Catelani, F. D'Andrea, F. De Rensis, Tetrahedron 1997, 53, 8665-8674.
- (1997) Tetrahedron , vol.53 , pp. 8665-8674
- Barili, P.L.¹ Berti, G.² Catelani, G.³ D'Andrea, F.⁴ De Rensis, F.⁵

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