SYNTHESIS OF BLOOD-GROUP SUBSTANCES .8. SYNTHESIS OF THE BRANCHED TRISACCHARIDE 2-ACETAMIDO-2-DEOXY-4-ORTHO-(ALPHA-L-FUCOPYRANOSYL)-3-ORTHO-(BETA-D-GALACTOPYRANOSYL)-D-GLUCOPYRANOSE

被引：23

作者：

JACQUINET, JC ^{[1
]}

SINAY, P ^{[1
]}

机构：

[1] UER SCI FONDAMENTALES & APPL,BIOCHIM STRUCT LAB,F-45045 ORLEANS,FRANCE

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 02期

关键词：

D O I：

10.1039/p19790000319

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide with benzyl 2-acetamido-4-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside provided crystalline benzyl 2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D- galacto-pyranosyl)-4-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside in 87% yield. Deallylation followed by condensation with 1-O-(N-methyl)acetimidyl-2,3, 4-tri-O-benzyl-β-L-fucopyranose provided the crystalline derivative (13). The title trisaccharide was obtained after O-deacetylation followed by catalytic hydrogenolysis. Preparations of 2-acetamido-2-deoxy-3-O-(β-D- galactopyranosyl)-D-glucopyranose and 2-acetamido-2-deoxy-4-O-(α-L- fucopyranosyl)-D-glucopyranose are reported.

引用

页码：319 / 322

页数：4

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