p-Nitrophenyl group for anomeric protection of oligosaccharides, selective oxidative cleavage via p-acetamidophenyl glycosides

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3343-3344

  Fukase, Koichi ^a   Yasukochi, Takashi ^a   Nakai, Yoshihiko ^a   Kusumoto, Shoichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029968534     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00507-2     Document Type: Article

References (12)

1. (a) Nilsson, K. G. I. Carbohydr. Res. 1989, 188, 9-17.
2. (b) Look, G. C.; Wong, C.-H. Tetrahedron Lett. 1992, 33, 4253-4256.
3. (c) Binder, W. H.; Kählig, H.; Schmid, W. Tetrahedron 1994, 50, 10407-10418.
4. (d) López, R.; Fernández-Mayoralas, A. Tetrahedron Lett. 1992, 33, 5449-5452.
5. (e) Löpez, R.; Fernández-Mayoralas, A. J. Org. Chem. 1994, 59, 737-745.
6. (f) Usui, T.; Murata, T.; Yabuuchi, Y.; Ogawa, K. Carbohydr. Res. 1993, 250, 57-66.
7. (g) Matahira, Y.; Ohno, K.; Kawaguchi, M.; Kawagishi, H.; Usui, T. J. Carbohydr. Chem. 1995, 14, 213-225.
8. Fukase, K.; Tanaka, H.; Torii, S.; Kusumoto, K. Tetrahedron Lett. 1990, 31, 389-392.
9. (a) Fukuyama, T.; Laird, A. A.; Hotchkiss, L. M. Tetrahedron Lett. 1985, 26, 6291-6292.
10. (b) Petitou, M.; Duchaussoy, P.; Choay, J. Tetrahedron Lett. 1988, 29, 1389-1390.
11. 1d
12. The direct oxidative cleavage of a p-aminophenyl glycoside with CAN also proceeded satisfactorily. However, isolation of the product from the many by-products formed by oxidation of the p-aminophenyl moiety was then very difficult.