Synthesis of 2-deoxy and 2,6-dideoxy glycosides under neutral conditions in LiClO4/Et2O mixtures

Chemical Communications

Volumn , Issue 24, 1998, Pages 2759-2760

  Schene, Heidrun ^a   Waldmann, Herbert ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKYLATING AGENT; DEOXYSUGAR; ETHYLENE OXIDE; GLYCOSIDASE; GLYCOSIDE; HEAVY METAL; LITHIUM DERIVATIVE;

ARTICLE; PH; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032556779     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807734g     Document Type: Article

References (33)

1. J. Thiem and W. Klaffke, Top. Curr. Chem., 1990, 154, 285; K. Toshima and K. Tatsuta, Chem. Rev., 1993, 93, 1503.
2. J. Thiem and W. Klaffke, Top. Curr. Chem., 1990, 154, 285; K. Toshima and K. Tatsuta, Chem. Rev., 1993, 93, 1503.
3. For recent references see: J. Thiem and W. Klaffke, J. Org. Chem., 1989, 54, 2006; S. Sabesan and S. Neira, J. Org. Chem., 1991, 56, 5468; K. Suzuki, G. A. Sulikowski, R. W. Friesen and S. J. Danishefsky, J. Am. Chem. Soc., 1990, 112, 8895; H. Mereyala, V. R. Kulkarni, D. Ravi, G. V. M. Sharma, B. Venkateswara Rao and G. B. Reddy, Tetrahedron Lett., 1992, 48, 545; K. Toshima, S. Mukaiyma, Y. Nozaki, H. Inokachi, M. Nakata and K Tatsuta, J. Am. Chem. Soc., 1994, 116, 9042;
4. For recent references see: J. Thiem and W. Klaffke, J. Org. Chem., 1989, 54, 2006; S. Sabesan and S. Neira, J. Org. Chem., 1991, 56, 5468; K. Suzuki, G. A. Sulikowski, R. W. Friesen and S. J. Danishefsky, J. Am. Chem. Soc., 1990, 112, 8895; H. Mereyala, V. R. Kulkarni, D. Ravi, G. V. M. Sharma, B. Venkateswara Rao and G. B. Reddy, Tetrahedron Lett., 1992, 48, 545; K. Toshima, S. Mukaiyma, Y. Nozaki, H. Inokachi, M. Nakata and K Tatsuta, J. Am. Chem. Soc., 1994, 116, 9042;
5. For recent references see: J. Thiem and W. Klaffke, J. Org. Chem., 1989, 54, 2006; S. Sabesan and S. Neira, J. Org. Chem., 1991, 56, 5468; K. Suzuki, G. A. Sulikowski, R. W. Friesen and S. J. Danishefsky, J. Am. Chem. Soc., 1990, 112, 8895; H. Mereyala, V. R. Kulkarni, D. Ravi, G. V. M. Sharma, B. Venkateswara Rao and G. B. Reddy, Tetrahedron Lett., 1992, 48, 545; K. Toshima, S. Mukaiyma, Y. Nozaki, H. Inokachi, M. Nakata and K Tatsuta, J. Am. Chem. Soc., 1994, 116, 9042;
6. For recent references see: J. Thiem and W. Klaffke, J. Org. Chem., 1989, 54, 2006; S. Sabesan and S. Neira, J. Org. Chem., 1991, 56, 5468; K. Suzuki, G. A. Sulikowski, R. W. Friesen and S. J. Danishefsky, J. Am. Chem. Soc., 1990, 112, 8895; H. Mereyala, V. R. Kulkarni, D. Ravi, G. V. M. Sharma, B. Venkateswara Rao and G. B. Reddy, Tetrahedron Lett., 1992, 48, 545; K. Toshima, S. Mukaiyma, Y. Nozaki, H. Inokachi, M. Nakata and K Tatsuta, J. Am. Chem. Soc., 1994, 116, 9042;
7. For recent references see: J. Thiem and W. Klaffke, J. Org. Chem., 1989, 54, 2006; S. Sabesan and S. Neira, J. Org. Chem., 1991, 56, 5468; K. Suzuki, G. A. Sulikowski, R. W. Friesen and S. J. Danishefsky, J. Am. Chem. Soc., 1990, 112, 8895; H. Mereyala, V. R. Kulkarni, D. Ravi, G. V. M. Sharma, B. Venkateswara Rao and G. B. Reddy, Tetrahedron Lett., 1992, 48, 545; K. Toshima, S. Mukaiyma, Y. Nozaki, H. Inokachi, M. Nakata and K Tatsuta, J. Am. Chem. Soc., 1994, 116, 9042;
8. For recent references see: J. Thiem, M. Gerken and K. Bock, Liebigs Ann. Chem., 1983, 462; Y. Ito and T. Ogawa, Tetrahedron Lett., 1990, 46, 89; K. Toshima, Y. Nozaki and K. Tatsuta, Tetrahedron Lett., 1991, 32, 6887; R. Preuss and R. R. Schmidt, Synthesis, 1988, 694; S. Hashimoto, Y. Yanagiya, T. Honda and S. Ikegami, Chem. Lett., 1992, 1511.
9. For recent references see: J. Thiem, M. Gerken and K. Bock, Liebigs Ann. Chem., 1983, 462; Y. Ito and T. Ogawa, Tetrahedron Lett., 1990, 46, 89; K. Toshima, Y. Nozaki and K. Tatsuta, Tetrahedron Lett., 1991, 32, 6887; R. Preuss and R. R. Schmidt, Synthesis, 1988, 694; S. Hashimoto, Y. Yanagiya, T. Honda and S. Ikegami, Chem. Lett., 1992, 1511.
10. For recent references see: J. Thiem, M. Gerken and K. Bock, Liebigs Ann. Chem., 1983, 462; Y. Ito and T. Ogawa, Tetrahedron Lett., 1990, 46, 89; K. Toshima, Y. Nozaki and K. Tatsuta, Tetrahedron Lett., 1991, 32, 6887; R. Preuss and R. R. Schmidt, Synthesis, 1988, 694; S. Hashimoto, Y. Yanagiya, T. Honda and S. Ikegami, Chem. Lett., 1992, 1511.
11. For recent references see: J. Thiem, M. Gerken and K. Bock, Liebigs Ann. Chem., 1983, 462; Y. Ito and T. Ogawa, Tetrahedron Lett., 1990, 46, 89; K. Toshima, Y. Nozaki and K. Tatsuta, Tetrahedron Lett., 1991, 32, 6887; R. Preuss and R. R. Schmidt, Synthesis, 1988, 694; S. Hashimoto, Y. Yanagiya, T. Honda and S. Ikegami, Chem. Lett., 1992, 1511.
12. For recent references see: J. Thiem, M. Gerken and K. Bock, Liebigs Ann. Chem., 1983, 462; Y. Ito and T. Ogawa, Tetrahedron Lett., 1990, 46, 89; K. Toshima, Y. Nozaki and K. Tatsuta, Tetrahedron Lett., 1991, 32, 6887; R. Preuss and R. R. Schmidt, Synthesis, 1988, 694; S. Hashimoto, Y. Yanagiya, T. Honda and S. Ikegami, Chem. Lett., 1992, 1511.
13. J. Gervay and S. Danishefsky, J. Org. Chem., 1991, 56, 5448.
14. Recent references: application of the Koenigs - Knorr reaction in the direct synthesis of 2-deoxy glycosides employing the insoluble silver silicate: (a) J. Thiem and S. Köpper, Tetrahedron, 1990, 46, 133;
15. (b) R. W. Binkley, J. Carbohydr. Chem., 1990,9, 507; application of glycosyl phosphoramidites and phosphites for the direct synthesis of 2-deoxy glycosides:
16. H. Li, M. Chem and K. Zhao, Tetrahedron Lett., 1997, 38, 6143;
17. S. Hashimoto, A. Sano, H. Sakamoto, M. Nakajima, Y Yanagiya and S. Ikegami, Synlett, 1995, 1271; application of glycosyl sulfoxides for the direct synthesis of 2-deoxy glycosides:
18. (e) S.-H. Kim, D. Augeri, D. Yang and D. Kahne, J. Am. Chem. Soc., 1994, 116, 1766; application of gylcosyl fluorides for the direct synthesis of 2-deoxy glycosides:
19. (f) J. Junnmann, I. Lundt and J. Thiem, Liebigs Ann. Chem., 1991, 759.
20. H. Waldmann, G. Böhm, U. Schmid and H. Röttele, Angew. Chem., 1994, 106, 2024; Angew. Chem., Int. Ed. Engl., 1994, 33, 1944; G. Böhm and H. Waldmann, Tetrahedron Lett., 1995, 36, 3843; G. Böhm and H. Waldmann, Liebigs. Ann. Chem., 1996, 613 and 621; U. Schmid and H. Waldmann, Chem. Eur. J., 1998, 4, 494; H. Schene and H. Waldmann, Eur. J. Org. Chem., 1998, 1227.
21. H. Waldmann, G. Böhm, U. Schmid and H. Röttele, Angew. Chem., 1994, 106, 2024; Angew. Chem., Int. Ed. Engl., 1994, 33, 1944; G. Böhm and H. Waldmann, Tetrahedron Lett., 1995, 36, 3843; G. Böhm and H. Waldmann, Liebigs. Ann. Chem., 1996, 613 and 621; U. Schmid and H. Waldmann, Chem. Eur. J., 1998, 4, 494; H. Schene and H. Waldmann, Eur. J. Org. Chem., 1998, 1227.
22. H. Waldmann, G. Böhm, U. Schmid and H. Röttele, Angew. Chem., 1994, 106, 2024; Angew. Chem., Int. Ed. Engl., 1994, 33, 1944; G. Böhm and H. Waldmann, Tetrahedron Lett., 1995, 36, 3843; G. Böhm and H. Waldmann, Liebigs. Ann. Chem., 1996, 613 and 621; U. Schmid and H. Waldmann, Chem. Eur. J., 1998, 4, 494; H. Schene and H. Waldmann, Eur. J. Org. Chem., 1998, 1227.
23. H. Waldmann, G. Böhm, U. Schmid and H. Röttele, Angew. Chem., 1994, 106, 2024; Angew. Chem., Int. Ed. Engl., 1994, 33, 1944; G. Böhm and H. Waldmann, Tetrahedron Lett., 1995, 36, 3843; G. Böhm and H. Waldmann, Liebigs. Ann. Chem., 1996, 613 and 621; U. Schmid and H. Waldmann, Chem. Eur. J., 1998, 4, 494; H. Schene and H. Waldmann, Eur. J. Org. Chem., 1998, 1227.
24. H. Waldmann, G. Böhm, U. Schmid and H. Röttele, Angew. Chem., 1994, 106, 2024; Angew. Chem., Int. Ed. Engl., 1994, 33, 1944; G. Böhm and H. Waldmann, Tetrahedron Lett., 1995, 36, 3843; G. Böhm and H. Waldmann, Liebigs. Ann. Chem., 1996, 613 and 621; U. Schmid and H. Waldmann, Chem. Eur. J., 1998, 4, 494; H. Schene and H. Waldmann, Eur. J. Org. Chem., 1998, 1227.
25. H. Waldmann, G. Böhm, U. Schmid and H. Röttele, Angew. Chem., 1994, 106, 2024; Angew. Chem., Int. Ed. Engl., 1994, 33, 1944; G. Böhm and H. Waldmann, Tetrahedron Lett., 1995, 36, 3843; G. Böhm and H. Waldmann, Liebigs. Ann. Chem., 1996, 613 and 621; U. Schmid and H. Waldmann, Chem. Eur. J., 1998, 4, 494; H. Schene and H. Waldmann, Eur. J. Org. Chem., 1998, 1227.
26. 2 according to the general procedure (W. Rosenbrook, Jr., D. A. Riley and P. A. Lartey, Tetrahedron Lett., 1985, 26, 3).
27. 2 according to the general procedure (W. Rosenbrook, Jr., D. A. Riley and P. A. Lartey, Tetrahedron Lett., 1985, 26, 3).
28. S. T. Handy, P. A. Grieco, C. Mineur and L. Ghosez, Synlett 1995, 565; R. Tamion, C. Mineur and L. Ghosez, Tetrahedron Lett., 1995, 36, 8977.
29. S. T. Handy, P. A. Grieco, C. Mineur and L. Ghosez, Synlett 1995, 565; R. Tamion, C. Mineur and L. Ghosez, Tetrahedron Lett., 1995, 36, 8977.
30. P. A. Grieco, Aldrichim. Acta, 1991, 24, 59; H. Waldmann, Angew. Chem., 1991, 103, 1335; Angew. Chem., Int. Ed. Engl., 1991, 30, 1306; U. Schmid and H. Waldmann, in Organic Synthesis Highlights III, ed. J. Mulzer and H. Waldmann, Wiley-VCH, Weinheim, 1997, pp. 205-210
31. P. A. Grieco, Aldrichim. Acta, 1991, 24, 59; H. Waldmann, Angew. Chem., 1991, 103, 1335; Angew. Chem., Int. Ed. Engl., 1991, 30, 1306; U. Schmid and H. Waldmann, in Organic Synthesis Highlights III, ed. J. Mulzer and H. Waldmann, Wiley-VCH, Weinheim, 1997, pp. 205-210
32. P. A. Grieco, Aldrichim. Acta, 1991, 24, 59; H. Waldmann, Angew. Chem., 1991, 103, 1335; Angew. Chem., Int. Ed. Engl., 1991, 30, 1306; U. Schmid and H. Waldmann, in Organic Synthesis Highlights III, ed. J. Mulzer and H. Waldmann, Wiley-VCH, Weinheim, 1997, pp. 205-210
33. P. A. Grieco, Aldrichim. Acta, 1991, 24, 59; H. Waldmann, Angew. Chem., 1991, 103, 1335; Angew. Chem., Int. Ed. Engl., 1991, 30, 1306; U. Schmid and H. Waldmann, in Organic Synthesis Highlights III, ed. J. Mulzer and H. Waldmann, Wiley-VCH, Weinheim, 1997, pp. 205-210