Strategic approach to C-nucleosides via sugar anomeric radical, cation, and anion with sugar tellurides

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5541-5544

  He, Wei ^a   Togo, Hideo ^a   Yokoyama, Masataka ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

C NUCLEOSIDE; CARBOHYDRATE DERIVATIVE; TELLURIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030792356     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01196-9     Document Type: Article

References (34)

1. (a) reviews: Suhadalnik, R. J., Nucleoside Antibiotics, Wiley-Interscience: New York, 1970; Mizuno, Y. The Organic Chemistry of Nucleosides and Nucleotides, Townsend, L. B. Ed.; Plenum: New York, 1988; Matsuda, A. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 907-920; Nishiyama, S.; Yamamura, S. ibid. 1991, 49, 670-681; Sato, T.; Noyori, R. ibid. 1980, 38, 862-879; Sato, T.; Noyori, R. Ibid. 1980, 38, 947-966; Watanabe, K. A. Ibid. 1987, 45, 212-231; Katagiri, N. Ibid. 1989, 47, 707-721; Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; Watanabe, K. A. The Chemistry of C-Nucleosides in Chemistry of Nucleosides and Nucleotides, Vol. 3; Townsend, L. B. Ed.; Plenum Press: New York, 1994, pp. 421-535.
2. (a) reviews: Suhadalnik, R. J., Nucleoside Antibiotics, Wiley-Interscience: New York, 1970; Mizuno, Y. The Organic Chemistry of Nucleosides and Nucleotides, Townsend, L. B. Ed.; Plenum: New York, 1988; Matsuda, A. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 907-920; Nishiyama, S.; Yamamura, S. ibid. 1991, 49, 670-681; Sato, T.; Noyori, R. ibid. 1980, 38, 862-879; Sato, T.; Noyori, R. Ibid. 1980, 38, 947-966; Watanabe, K. A. Ibid. 1987, 45, 212-231; Katagiri, N. Ibid. 1989, 47, 707-721; Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; Watanabe, K. A. The Chemistry of C-Nucleosides in Chemistry of Nucleosides and Nucleotides, Vol. 3; Townsend, L. B. Ed.; Plenum Press: New York, 1994, pp. 421-535.
3. (a) reviews: Suhadalnik, R. J., Nucleoside Antibiotics, Wiley-Interscience: New York, 1970; Mizuno, Y. The Organic Chemistry of Nucleosides and Nucleotides, Townsend, L. B. Ed.; Plenum: New York, 1988; Matsuda, A. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 907-920; Nishiyama, S.; Yamamura, S. ibid. 1991, 49, 670-681; Sato, T.; Noyori, R. ibid. 1980, 38, 862-879; Sato, T.; Noyori, R. Ibid. 1980, 38, 947-966; Watanabe, K. A. Ibid. 1987, 45, 212-231; Katagiri, N. Ibid. 1989, 47, 707-721; Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; Watanabe, K. A. The Chemistry of C-Nucleosides in Chemistry of Nucleosides and Nucleotides, Vol. 3; Townsend, L. B. Ed.; Plenum Press: New York, 1994, pp. 421-535.
4. (a) reviews: Suhadalnik, R. J., Nucleoside Antibiotics, Wiley-Interscience: New York, 1970; Mizuno, Y. The Organic Chemistry of Nucleosides and Nucleotides, Townsend, L. B. Ed.; Plenum: New York, 1988; Matsuda, A. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 907-920; Nishiyama, S.; Yamamura, S. ibid. 1991, 49, 670-681; Sato, T.; Noyori, R. ibid. 1980, 38, 862-879; Sato, T.; Noyori, R. Ibid. 1980, 38, 947-966; Watanabe, K. A. Ibid. 1987, 45, 212-231; Katagiri, N. Ibid. 1989, 47, 707-721; Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; Watanabe, K. A. The Chemistry of C-Nucleosides in Chemistry of Nucleosides and Nucleotides, Vol. 3; Townsend, L. B. Ed.; Plenum Press: New York, 1994, pp. 421-535.
5. (a) reviews: Suhadalnik, R. J., Nucleoside Antibiotics, Wiley-Interscience: New York, 1970; Mizuno, Y. The Organic Chemistry of Nucleosides and Nucleotides, Townsend, L. B. Ed.; Plenum: New York, 1988; Matsuda, A. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 907-920; Nishiyama, S.; Yamamura, S. ibid. 1991, 49, 670-681; Sato, T.; Noyori, R. ibid. 1980, 38, 862-879; Sato, T.; Noyori, R. Ibid. 1980, 38, 947-966; Watanabe, K. A. Ibid. 1987, 45, 212-231; Katagiri, N. Ibid. 1989, 47, 707-721; Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; Watanabe, K. A. The Chemistry of C-Nucleosides in Chemistry of Nucleosides and Nucleotides, Vol. 3; Townsend, L. B. Ed.; Plenum Press: New York, 1994, pp. 421-535.
6. (a) reviews: Suhadalnik, R. J., Nucleoside Antibiotics, Wiley-Interscience: New York, 1970; Mizuno, Y. The Organic Chemistry of Nucleosides and Nucleotides, Townsend, L. B. Ed.; Plenum: New York, 1988; Matsuda, A. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 907-920; Nishiyama, S.; Yamamura, S. ibid. 1991, 49, 670-681; Sato, T.; Noyori, R. ibid. 1980, 38, 862-879; Sato, T.; Noyori, R. Ibid. 1980, 38, 947-966; Watanabe, K. A. Ibid. 1987, 45, 212-231; Katagiri, N. Ibid. 1989, 47, 707-721; Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; Watanabe, K. A. The Chemistry of C-Nucleosides in Chemistry of Nucleosides and Nucleotides, Vol. 3; Townsend, L. B. Ed.; Plenum Press: New York, 1994, pp. 421-535.
7. (a) reviews: Suhadalnik, R. J., Nucleoside Antibiotics, Wiley-Interscience: New York, 1970; Mizuno, Y. The Organic Chemistry of Nucleosides and Nucleotides, Townsend, L. B. Ed.; Plenum: New York, 1988; Matsuda, A. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 907-920; Nishiyama, S.; Yamamura, S. ibid. 1991, 49, 670-681; Sato, T.; Noyori, R. ibid. 1980, 38, 862-879; Sato, T.; Noyori, R. Ibid. 1980, 38, 947-966; Watanabe, K. A. Ibid. 1987, 45, 212-231; Katagiri, N. Ibid. 1989, 47, 707-721; Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; Watanabe, K. A. The Chemistry of C-Nucleosides in Chemistry of Nucleosides and Nucleotides, Vol. 3; Townsend, L. B. Ed.; Plenum Press: New York, 1994, pp. 421-535.
8. (a) reviews: Suhadalnik, R. J., Nucleoside Antibiotics, Wiley-Interscience: New York, 1970; Mizuno, Y. The Organic Chemistry of Nucleosides and Nucleotides, Townsend, L. B. Ed.; Plenum: New York, 1988; Matsuda, A. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 907-920; Nishiyama, S.; Yamamura, S. ibid. 1991, 49, 670-681; Sato, T.; Noyori, R. ibid. 1980, 38, 862-879; Sato, T.; Noyori, R. Ibid. 1980, 38, 947-966; Watanabe, K. A. Ibid. 1987, 45, 212-231; Katagiri, N. Ibid. 1989, 47, 707-721; Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; Watanabe, K. A. The Chemistry of C-Nucleosides in Chemistry of Nucleosides and Nucleotides, Vol. 3; Townsend, L. B. Ed.; Plenum Press: New York, 1994, pp. 421-535.
9. (a) reviews: Suhadalnik, R. J., Nucleoside Antibiotics, Wiley-Interscience: New York, 1970; Mizuno, Y. The Organic Chemistry of Nucleosides and Nucleotides, Townsend, L. B. Ed.; Plenum: New York, 1988; Matsuda, A. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 907-920; Nishiyama, S.; Yamamura, S. ibid. 1991, 49, 670-681; Sato, T.; Noyori, R. ibid. 1980, 38, 862-879; Sato, T.; Noyori, R. Ibid. 1980, 38, 947-966; Watanabe, K. A. Ibid. 1987, 45, 212-231; Katagiri, N. Ibid. 1989, 47, 707-721; Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; Watanabe, K. A. The Chemistry of C-Nucleosides in Chemistry of Nucleosides and Nucleotides, Vol. 3; Townsend, L. B. Ed.; Plenum Press: New York, 1994, pp. 421-535.
10. (a) reviews: Suhadalnik, R. J., Nucleoside Antibiotics, Wiley-Interscience: New York, 1970; Mizuno, Y. The Organic Chemistry of Nucleosides and Nucleotides, Townsend, L. B. Ed.; Plenum: New York, 1988; Matsuda, A. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 907-920; Nishiyama, S.; Yamamura, S. ibid. 1991, 49, 670-681; Sato, T.; Noyori, R. ibid. 1980, 38, 862-879; Sato, T.; Noyori, R. Ibid. 1980, 38, 947-966; Watanabe, K. A. Ibid. 1987, 45, 212-231; Katagiri, N. Ibid. 1989, 47, 707-721; Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; Watanabe, K. A. The Chemistry of C-Nucleosides in Chemistry of Nucleosides and Nucleotides, Vol. 3; Townsend, L. B. Ed.; Plenum Press: New York, 1994, pp. 421-535.
11. (a) reviews: Suhadalnik, R. J., Nucleoside Antibiotics, Wiley-Interscience: New York, 1970; Mizuno, Y. The Organic Chemistry of Nucleosides and Nucleotides, Townsend, L. B. Ed.; Plenum: New York, 1988; Matsuda, A. Yuki Gosei Kagaku Kyokai Shi 1990, 48, 907-920; Nishiyama, S.; Yamamura, S. ibid. 1991, 49, 670-681; Sato, T.; Noyori, R. ibid. 1980, 38, 862-879; Sato, T.; Noyori, R. Ibid. 1980, 38, 947-966; Watanabe, K. A. Ibid. 1987, 45, 212-231; Katagiri, N. Ibid. 1989, 47, 707-721; Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; Watanabe, K. A. The Chemistry of C-Nucleosides in Chemistry of Nucleosides and Nucleotides, Vol. 3; Townsend, L. B. Ed.; Plenum Press: New York, 1994, pp. 421-535.
12. (b) papers: Chaudhuri, N. C.; Kool, E. T. Tetrahedron Lett. 1995, 36, 1795-1798; Xiang, Y.; Teng, Q.; Chu, C. K. ibid. 1995, 36, 3781-3784; Horenstein, B. A.; Zabinski, R. F.; Schramm, V. L. ibid. 1993, 34, 7213-7216; Watanabe, T.; Nishiyama, S.; Yamamura, S.; Kato, K.; Nagai, M.; Takita, T. ibid. 1991, 32, 2399-2400; Patil, S. A.; Otter, B. A.; Klein, R. S. ibid. 1994, 35, 5339-5342; Harusawa, S.; Murai, Y.; Moriyama, H.; Ohishi, H.; Yoneda, R.; Kurihara, T. ibid. 1995, 36, 3165-3168; Gudmundsson, K. S.; Drach, J. C.; Townsend, L. B. ibid. 1996, 37, 2365-2368; Hsieh, H-P.; MeLaughlin, L. W. J. Org. Chem. 1995, 60, 5356-5359.
13. (b) papers: Chaudhuri, N. C.; Kool, E. T. Tetrahedron Lett. 1995, 36, 1795-1798; Xiang, Y.; Teng, Q.; Chu, C. K. ibid. 1995, 36, 3781-3784; Horenstein, B. A.; Zabinski, R. F.; Schramm, V. L. ibid. 1993, 34, 7213-7216; Watanabe, T.; Nishiyama, S.; Yamamura, S.; Kato, K.; Nagai, M.; Takita, T. ibid. 1991, 32, 2399-2400; Patil, S. A.; Otter, B. A.; Klein, R. S. ibid. 1994, 35, 5339-5342; Harusawa, S.; Murai, Y.; Moriyama, H.; Ohishi, H.; Yoneda, R.; Kurihara, T. ibid. 1995, 36, 3165-3168; Gudmundsson, K. S.; Drach, J. C.; Townsend, L. B. ibid. 1996, 37, 2365-2368; Hsieh, H-P.; MeLaughlin, L. W. J. Org. Chem. 1995, 60, 5356-5359.
14. (b) papers: Chaudhuri, N. C.; Kool, E. T. Tetrahedron Lett. 1995, 36, 1795-1798; Xiang, Y.; Teng, Q.; Chu, C. K. ibid. 1995, 36, 3781-3784; Horenstein, B. A.; Zabinski, R. F.; Schramm, V. L. ibid. 1993, 34, 7213-7216; Watanabe, T.; Nishiyama, S.; Yamamura, S.; Kato, K.; Nagai, M.; Takita, T. ibid. 1991, 32, 2399-2400; Patil, S. A.; Otter, B. A.; Klein, R. S. ibid. 1994, 35, 5339-5342; Harusawa, S.; Murai, Y.; Moriyama, H.; Ohishi, H.; Yoneda, R.; Kurihara, T. ibid. 1995, 36, 3165-3168; Gudmundsson, K. S.; Drach, J. C.; Townsend, L. B. ibid. 1996, 37, 2365-2368; Hsieh, H-P.; MeLaughlin, L. W. J. Org. Chem. 1995, 60, 5356-5359.
15. (b) papers: Chaudhuri, N. C.; Kool, E. T. Tetrahedron Lett. 1995, 36, 1795-1798; Xiang, Y.; Teng, Q.; Chu, C. K. ibid. 1995, 36, 3781-3784; Horenstein, B. A.; Zabinski, R. F.; Schramm, V. L. ibid. 1993, 34, 7213-7216; Watanabe, T.; Nishiyama, S.; Yamamura, S.; Kato, K.; Nagai, M.; Takita, T. ibid. 1991, 32, 2399-2400; Patil, S. A.; Otter, B. A.; Klein, R. S. ibid. 1994, 35, 5339-5342; Harusawa, S.; Murai, Y.; Moriyama, H.; Ohishi, H.; Yoneda, R.; Kurihara, T. ibid. 1995, 36, 3165-3168; Gudmundsson, K. S.; Drach, J. C.; Townsend, L. B. ibid. 1996, 37, 2365-2368; Hsieh, H-P.; MeLaughlin, L. W. J. Org. Chem. 1995, 60, 5356-5359.
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