Synthesis of the β-methyl glycoside of lacto-N-fucopentaose III

被引：24

作者：

Zhang, YM ^{[1
]}

Esnault, J ^{[1
]}

Mallet, JM ^{[1
]}

Sinaÿ, P ^{[1
]}

机构：

[1] Ecole Normale Super, Dept Chim, CNRS, F-75231 Paris 05, France

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1999年 / 18卷 / 04期

关键词：

D O I：

10.1080/07328309908544006

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：

A total synthesis of the beta-methyl glycoside of lacto-N-fucopentaose III (1) is described. Phenyl 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1-->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside (4), a key intermediate prepared by condensation of 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl bromide (2) and phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside (3), was glycosylated with ethyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside (5) to give the trisaccharide donor 6, which, on coupling with methyl 2,6-di-O-benzyl-beta-D-galactopyranosyl-(1-->4)2,3,6-tri-O-benzyl-beta-D-glucopyranoside (7), afforded the pentasaccharide 8. It was easily transformed into the target pentasaccharide 1 via hydrazinolysis, acetylation, O-deacetylation, and hydrogenolysis.

引用

页码：419 / 427

页数：9

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