Glycosyl phosphonium halide as a reactive intermediate in highly α-selective glycosylation

Bulletin of the Chemical Society of Japan

Volumn 78, Issue 5, 2005, Pages 910-916

  Kobashi, Yohei ^a   Mukaiyama, Teruaki ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OXIDES; SYNTHESIS (CHEMICAL);

GLYCOSYL PHOSPHONIUM HALIDES; PHOSPHINE OXIDES; REFLUXING;

POLYSACCHARIDES;

2,3,4,6 TETRA O BENZYL DEXTRO GLUCOPYRANOSYL BROMIDE; BROMINE DERIVATIVE; DISACCHARIDE; GLYCOSYLPHOSPHONIUM HALIDE; HALIDE; PHOSPHINE OXIDE DERIVATIVE; TRIS(1 PYRROLIDINO)PHOSPHINE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; GLYCOSYLATION; ROOM TEMPERATURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 20344403548     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.78.910     Document Type: Article

References (32)

1. Reviews on glycosylations: a) H. Paulsen, Angew. Chem., Int. Ed. Engl, 21, 155 (1982).
2. b) R. R. Schmidt, Angew. Chem., Int. Ed. Engl., 25, 212 (1986).
3. c) H. Kuntz, Angew. Chem., Int. Ed. Engl., 26, 294 (1987).
4. d) P. Sinaÿ, Pure Appl. Chem., 63, 519 (1991).
5. e) K. Suzuki and T. Nagasawa, J. Synth. Org. Chem., Jpn., 50, 378 (1992).
6. f) K. Toshima and K. Tatsuta, Chem. Rev., 93, 1503 (1993).
7. g) B. Ernst, G. W. Hart, and P. Sinaÿ, "Carbohydrate in Chemistry and Biology," WILEY-VCH, Weinheim etc. (2000), Part 1.
8. h) K. J. Jensen, J. Chem. Soc., Perkin Trans. 1, 2002, 2219.
9. i) A. V. Demchenko, Synlett, 2003, 1225.
10. T. K. Lindhorst, "Essentials of Carbohydrate Chemistry and Biochemistry," WILEY-VCH (2003).
11. R. U. Lemieux, K. B. Hendriks, R. V. Stick, and K. James, J. Am. Chem. Soc., 97, 4056 (1975).
12. a) S. N. Lam and J. Gervay, Carbohydr. Res., 337, 1953 (2002).
13. b) A. K. Sarkar, A. K. Ray, and N. Roy, Carbohydr. Res., 190, 181 (1989).
14. c) A. Chernyak, S. Oscarson, and D. Turek, Carbohydr. Res., 329, 309 (2000).
15. a) J. W. Gillard and M. Israel, Tetrahedron Lett., 22, 513 (1981).
16. b) T. Ishikawa and H. G. Fletcher, Jr., J. Org. Chem., 34, 536 (1969).
17. M. Hadd and J. Gervay, Carbohydr. Res., 320, 61 (1999).
18. T. Mukaiyama, Y. Kobashi, and T. Shintou, Chem. Lett., 32, 900 (2003).
19. Molecular sieves 5A improved the yields of glycosylations using glycosyl phosphinite and iodomethane: see Ref. 7. Recent examples of glycosylation using molecular sieves: a) G. H. Posner and D. S. Bull, Tetrahedron Lett., 37, 6279 (1996).
20. b) K. Toshima, K. Kasumi, and S. Matsumura, Synlett, 1998, 643.
21. c) H. Jona, K. Takeuchi, and T. Mukaiyama, Chem. Lett., 2000, 1278.
22. d) K. Toshima, H. Nagai, K. Kasumi, K. Kawahara, and S. Matsumura, Tetrahedron, 60, 5331 (2004).
23. It is known to be a polar aprotic solvent with high electron-donating power: Y. Ozari and J. Jagur-Grodzinski, J. Chem. Soc., Chem. Commun., 1974, 295.
24. Reviews on glycosyl fluoride: a) M. Shimizu, H. Togo, and M. Yokoyama, Synthesis, 1998, 799.
25. b) M. Yokoyama, Carbohydr. Res., 327, 5 (2000).
26. c) K. Toshima, Carbohydr. Res., 327, 15 (2000).
27. d) T. Mukaiyama and H. Jona, Proc. Jpn. Acad., Ser. B, 78, 73 (2002).
28. 3P=O was δ 29.0 ppm).
29. L. D. Quin, "A Guide to Organophosphorous Chemistry," John Wiley and Sons (2000), p. 103.
30. H. Jona, H. Mandai, W. Chavasiri, K. Takeuchi, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 75, 291 (2002).
31. H. Chiba, S. Funasaka, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 76, 1629 (2003).
32. Analytical date of 16β has been reported from our group: T. Mukaiyama, K. Takeuchi, H. Jona, H. Maeshima, and T. Saitoh, Helv. Chim. Acta, 83, 1901 (2000).