Highly optimized β-mannosylation via p-methoxybenzyl assisted intramolecular aglycon delivery

Synlett

Volumn , Issue 10, 1998, Pages 1102-1104

  Ito, Yukishige ^a   Ohnishi, Yuki ^a   Ogawa, Tomoya ^a   Nakahara, Yoshiaki ^a,b  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b TOKAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003142999     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1894     Document Type: Article

References (27)

1. Y. Ito, T. Ogawa, Angew. Chem. Int. Ed. Engl. 1994, 33, 1765-1767,
2. Angew. Chem. 1994, 106, 1843-1845.
3. For recent publications, see; T. Iimori, H. Ohtake, S. Ikegami, Tetrahedron Lett. 1997, 38, 3415-3418;
4. G. Hodosi, P. Kovác, J. Am. Chem. Soc. 1997, 119, 2335-2336;
5. D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198-1199, and references cited therein.
6. For enzymatic approaches , see; G. M. Watt, L. Revers, M. C. Webberley, I. B. H. Willson, S. L. Flitsch, Angew. Chem. Int. Ed. Engl. 1997, 36, 2354-2356;
7. N. Taubken, B. Sauerbrei, J. Thiem, J. Carbohydr. Chem.1993, 12, 651-667;
8. S. Singh, M. Scigelova, D. H. G. Crout, Chem. Commun. 1996, 993-994.
9. F. Barresi, O. Hindsgaul, J. Am. Chem. Soc. 1991, 113, 9377-9379;
10. F. Barresi, O. Hindsgaul, Synlett 1992, 759-760;
11. G. Stork, G. Kim, J. Am. Chem. Soc. 1992, 114, 1087-1088;
12. G. Stork, J. J. La Clair, J. Am. Chem. Soc. 1996, 118, 247-248.
13. PMB group has been extensively used as a valuable hydroxy protecting group which can be removed by DDQ in water containing media: Y. Oikawa, T. Yoshioka, O. Yonemitsu, Tetrahedron Lett. 1982, 23, 885-888;
14. T. W. Greene, P. G. Wuts, Protective Croups in Organic Synthesis, 2nd ed., John Wiley & Sons, New York, 1991, p. 53.
15. (a) A. Dan, Y. Ito, T. Ogawa, J. Org. Chem. 1995, 60, 4680-4681.
16. (b) A. Dan, Y. Ito, T. Ogawa, Tetrahedron Lett. 1995, 36, 7487-7490.
17. (c) Y. Ito, T. Ogawa, J. Am. Chem. Soc. 1997, 119, 5562-5566.
18. Reaction of 4a and 4c with 11 afforded 60% (ref. 5a) and 29% yield (A. Dan, Y. Ito, T. Ogawa, unpublished) of corresponding β-manno glycoside, respectively.
19. T. Ogawa, K. Katano, M. Matsui, Carbohydr. Res. 1978, 64, C3-C9;
20. F. Yamazaki, S. Sato, T. Nukada, Y. Ito, T. Ogawa, Carbohydr. Res. 1990, 201, 31-50.
21. Y. Oikawa, T. Yoshioka, O. Yonemitsu, Tetrahedron Lett. 1982, 23, 889-892.
22. Preparation of 5 can be conveniently performed in 35 % overall yield from 7, without isolation of intermediates 8 and 9.
23. 1).
24. T. Nakano, Y. Ito, T. Ogawa, Carbohydr. Res. 1993, 243, 43-69,
25. H. Kuyama, Y. Nakahara, T. Nukada, Y. Ito, Y. Nakahara, T. Ogawa, Carbohydr. Res. 1993, 243, C1-C7.
26. H. Lönn, J. Carbohydr. Chem. 1987, 6, 301-306.
27. For a discussion on the role of 4,6-cyclic protection in β-mannosylation using glycosyl sulfoxide; see D. Crich, S. Sun, J. Am. Chem. Soc. 1997, 119, 11217-11223.