Efficient Preparation of Three Building Blocks for the Synthesis of Heparan Sulfate Fragments: Towards the Combinatorial Synthesis of Oligosaccharides from Hypervariable Regions

New, multigram routes to suitably protected L‐iduronyl monosaccharide donors 4 and 5 and 2‐azidoglucose acceptors 6 and 7 are described. The L‐iduronyl and D‐glucuronyl disaccharides 1−3 were then prepared from these compounds, by means of efficient and regioselective protective group manipulations....

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Bibliographic Details
Published in:European journal of organic chemistry 2003-09, Vol.2003 (18), p.3603-3620
Main Authors: Gavard, Ollivier, Hersant, Yaël, Alais, Jocelyne, Duverger, Véronique, Dilhas, Anna, Bascou, Alison, Bonnaffé, David
Format: Article
Language:English
Subjects:
Carbohydrates
Combinatorial chemistry
Glycosaminoglycans
Heparan sulfate
Heparin
Oligosaccharides
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Summary:New, multigram routes to suitably protected L‐iduronyl monosaccharide donors 4 and 5 and 2‐azidoglucose acceptors 6 and 7 are described. The L‐iduronyl and D‐glucuronyl disaccharides 1−3 were then prepared from these compounds, by means of efficient and regioselective protective group manipulations. These disaccharides form the basis of a combinatorial approach toward the synthesis of heparan sulfate fragments representative of the heterogeneous regions of this polysaccharide. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)Introduction
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200300254