8-O-sialylation of neuraminic acid acceptor reactivity and anomeric stereocontrol

被引：26

作者：

CastroPalomino, JC ^{[1
]}

Tsvetkov, YE ^{[1
]}

Schneider, R ^{[1
]}

Schmidt, RR ^{[1
]}

机构：

[1] UNIV KONSTANZ,FAK CHEM,D-78457 CONSTANCE,GERMANY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 39期

关键词：

D O I：

10.1016/S0040-4039(97)01620-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-O-Unprotected and 2-deoxy-2,3-dehydro-neuraminic acid derivatives 2, 4, and 10 exhibit enhanced acceptor properties at their 8-hydroxy group in sialylation reactions with phosphite 5 as donor; yet, mainly (10) or exclusively (2, 4) beta-glycoside bond formation was observed. The 3-phenylthionocarbonate group as stereodirecting auxiliary group in the sialyl donor 11 led with 10 as acceptor to exclusive formation of alpha(2-8)-linked disaccharide. (C) 1997 Published by Elsevier Science Ltd.

引用

页码：6837 / 6840

页数：4

共 23 条

[1]

CASTROPALOMINO JC, THESIS

[2]

HAKOMORI S, 1984, ANNU REV IMMUNOL, V2, P103, DOI 10.1146/annurev.immunol.2.1.103

[3] AN EFFICIENT APPROACH TO STEREOSELECTIVE GLYCOSYLATION OF N-ACETYLNEURAMINIC ACID - USE OF PHENYLSELENYL GROUP AS A STEREOCONTROLLING AUXILIARY [J].