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Synthesis of the Glc3Man N-glycan tetrasaccharide by iterative allyl IAD.

Authors
  • 1
Type
Published Article
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
341
Issue
10
Pages
1609–1618
Identifiers
PMID: 16529733
Source
Medline

Abstract

The synthesis of the tetrasaccharide alpha-D-Glcp-(1-->2)-alpha-D-Glcp-(1-->3)-alpha-D-Glcp-(1-->3)-alpha-D-Manp-OMe, corresponding to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved with complete stereocontrol by the use of iterative allyl protecting group mediated intramolecular aglycon delivery (allyl IAD) demonstrating the utility of intramolecular glycosylation for the stereocontrolled construction of multiple glycosidic linkages during the synthesis of an oligosaccharide.

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