Regio‐ and Stereocontrolled Synthesis of 2d‐Deoxy Lewis x Pentasaccharide

Abstract The total synthesis of 2d‐deoxy Lewis x pentasaccharide is described. Ethyl 2‐ O ‐acetyl‐3,4,6‐tri‐ O ‐benzyl‐1‐thio‐α,β‐ D ‐galactopyranoside was condensed with a diol of glucosamine to regio‐ and stereoselectively give the disaccharide, the C‐2′ position was then reduced after stereoselec...

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Published inEuropean journal of organic chemistry Vol. 2011; no. 35; pp. 7133 - 7139
Main Authors Zhang, Yanyan, Dong, Dengxiang, Qu, Huanhuan, Sollogoub, Matthieu, Zhang, Yongmin
Format Journal Article
LanguageEnglish
Published 01.12.2011
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Summary:Abstract The total synthesis of 2d‐deoxy Lewis x pentasaccharide is described. Ethyl 2‐ O ‐acetyl‐3,4,6‐tri‐ O ‐benzyl‐1‐thio‐α,β‐ D ‐galactopyranoside was condensed with a diol of glucosamine to regio‐ and stereoselectively give the disaccharide, the C‐2′ position was then reduced after stereoselective fucosylation to afford a Lewis x trisaccharide analogue. Regioselective glycosylation of a known lactoside diol with this trisaccharide provided a pentasaccharide that, after deprotection, gave the target pentasaccharide.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201101062