Synthesis of two Lewisx trisaccharides using regiospecific glycosylation reactions

被引：6

作者：

Mukherjee, D

Sarkar, SK

Chattopadhyay, P

Chowdhury, US

机构：

[1] Indian Inst Chem Biol, Synthet Biophys & Nat Prod Chem Div, Kolkata 700032, W Bengal, India

[2] Indian Inst Chem Biol, Dept Biol Chem, Kolkata 700032, W Bengal, India

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2005年 / 24卷 / 03期

关键词：

synthesis; trisaccharide; Lewis(x); N-iodosuccinimide; trifluoromethane-sulfonic acid;

D O I：

10.1081/CAR-200058529

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Synthesis of two Lewis(x) trisaccharides, namely, 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1 -> 4)-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-2-phthalimido-beta-D-glucopyranoside and 2-(trimethylsilyl)ethyl 2,3,4-tri-O-acetyl-6-O-t-butyldiphenylsilyl-beta-D-galactopyranosyl-(1 -> 4)-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-2-phthalimido-beta-D-glucopyranoside, has been achieved using a regiospecific glycosylation strategy under NIS-TfOH activation. Two trisaccharides were prepared from monosaccharides without any protecting group manipulation.

引用

页码：251 / 259

页数：9

共 28 条

[21] A concise synthesis of the 6-O- and 6′-O-sulfated analogues of the sialyl Lewis X tetrasaccharide [J].