Reaction and stereochemistry of C-glycosidation in 2-deoxy-4-thioribofuranoside

Chemistry Letters

Volumn , Issue 8, 1996, Pages 595-596

  Uenishi, Jun'ichi ^a   Sohma, Atsushi ^a   Yonemitsu, Osamu ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005627981     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.595     Document Type: Article

References (20)

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3. K. Toshima and K. Tatsuta, Chem. Rev. 93, 1503 (1993); R. R. Schmidt, in "Comprehensive Organic Synthesis" ed by B. M. Trost, Pergamon Press, Oxford, Vol. 6, p. 33 (1991).
4. S. F. Wnuk, Tetrahedron, 49, 9877 (1993), and references cited therein.
5. J. Uenishi, M. Motoyama, Y. Nishiyama, and S. Wakabayashi, J. Chem. Soc., Chem. Commun., 1991, 1421. M. R. Dyson, P. L. Coe, and R. T. Walker, J. Med. Chem., 34, 2782 (1991); J. A. Secrist III, K. N. Tiwari, J. M. Riodan, and J. A. Montgomery, J. Med. Chem., 34, 2361 (1991); J. Uenishi, K. Takahashi, M. Motoyama, H. Akashi, and T. Sasaki, Nucleosides & Nucelotides, 13, 1347 (1994).
6. J. Uenishi, M. Motoyama, Y. Nishiyama, and S. Wakabayashi, J. Chem. Soc., Chem. Commun., 1991, 1421. M. R. Dyson, P. L. Coe, and R. T. Walker, J. Med. Chem., 34, 2782 (1991); J. A. Secrist III, K. N. Tiwari, J. M. Riodan, and J. A. Montgomery, J. Med. Chem., 34, 2361 (1991); J. Uenishi, K. Takahashi, M. Motoyama, H. Akashi, and T. Sasaki, Nucleosides & Nucelotides, 13, 1347 (1994).
7. J. Uenishi, M. Motoyama, Y. Nishiyama, and S. Wakabayashi, J. Chem. Soc., Chem. Commun., 1991, 1421. M. R. Dyson, P. L. Coe, and R. T. Walker, J. Med. Chem., 34, 2782 (1991); J. A. Secrist III, K. N. Tiwari, J. M. Riodan, and J. A. Montgomery, J. Med. Chem., 34, 2361 (1991); J. Uenishi, K. Takahashi, M. Motoyama, H. Akashi, and T. Sasaki, Nucleosides & Nucelotides, 13, 1347 (1994).
8. J. Uenishi, M. Motoyama, Y. Nishiyama, and S. Wakabayashi, J. Chem. Soc., Chem. Commun., 1991, 1421. M. R. Dyson, P. L. Coe, and R. T. Walker, J. Med. Chem., 34, 2782 (1991); J. A. Secrist III, K. N. Tiwari, J. M. Riodan, and J. A. Montgomery, J. Med. Chem., 34, 2361 (1991); J. Uenishi, K. Takahashi, M. Motoyama, H. Akashi, and T. Sasaki, Nucleosides & Nucelotides, 13, 1347 (1994).
9. D. E. Levy and C. Tang, "The Chemistry of C-Glycosides" Tetrahedron Organic Chemistry Ser. Ser. ed by J. E. Baldwin and P. D. Magnus, Vol 13, Elsevier Sci. Ltd., Oxford (1995); M. H. D. Postema, "C-Glycoside Synthesis", Ser. ed by C. W. Rees, CRC Press, Boca Raton (1995).
10. D. E. Levy and C. Tang, "The Chemistry of C-Glycosides" Tetrahedron Organic Chemistry Ser. Ser. ed by J. E. Baldwin and P. D. Magnus, Vol 13, Elsevier Sci. Ltd., Oxford (1995); M. H. D. Postema, "C-Glycoside Synthesis", Ser. ed by C. W. Rees, CRC Press, Boca Raton (1995).
11. J. Uenishi, M. Motoyama, and K. Takahashi, Tetrahedron: Asymm., 5, 101 (1994).
12. This compound was derived from 2-deoxyribose in 3 steps by the standard method.
13. 4 (0.9 mmol) at -30°C, and the mixture was stirred at the same temperature for 15 to 30 min. Aqueous work up with sodium bicarbonate, extraction with ether, and purification by silica gel column chromatography gave compound 3-11.
14. 1H NMR.
15. 3SSi: 331.1764. Found: 331.1758.
16. Poor selectivity was reported for glycosidation in 2-deoxy 3-tert-butyldiphenylsilyloxy derivative; see T.-F. Yang, L. P. Kotra, Q. Teng, F. N. M. Naguib, J.-P. Sommadossi, M. el Kouni, and C. K. Chu, Tetrahedron Lett., 36, 983 (1995).
17. A few excellent stereocontrols in glycodsidation reaction were reported. Remote sterocontrol by the protecting group of the C-3 α-hydroxy function, see Y. Ichikawa, H. Kubota, K. Fujita, T. Okauchi, and K. Narasaka, Bull. Chem. Soc. Jpn., 62, 845 (1989); Lewis acid coordinated stereo control, see W.-B. Choi, L. J. Wilson, S. Yeola, D. C. Liotta, and R. F. Schinazi, J. Am. Chem. Soc., 113, 9377 (1991).
18. A few excellent stereocontrols in glycodsidation reaction were reported. Remote sterocontrol by the protecting group of the C-3 α-hydroxy function, see Y. Ichikawa, H. Kubota, K. Fujita, T. Okauchi, and K. Narasaka, Bull. Chem. Soc. Jpn., 62, 845 (1989); Lewis acid coordinated stereo control, see W.-B. Choi, L. J. Wilson, S. Yeola, D. C. Liotta, and R. F. Schinazi, J. Am. Chem. Soc., 113, 9377 (1991).
19. K. L. Dueholm and E. B. Pedersen, Synthesis, 1992, 1; recent example, A. Tse and T. S. Mansour, Tetrahedron Lett., 36, 7807 (1995).
20. K. L. Dueholm and E. B. Pedersen, Synthesis, 1992, 1; recent example, A. Tse and T. S. Mansour, Tetrahedron Lett., 36, 7807 (1995).