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

Authors
  • Attolino, Emanuele1
  • Cumpstey, Ian
  • Fairbanks, Antony J
  • 1 Chemistry Research Laboratory, Oxford University, Mansfield Road, Oxford OX1 3TA, UK.
Type
Published Article
Journal
Carbohydrate Research
Publisher
Elsevier
Publication Date
Jul 24, 2006
Volume
341
Issue
10
Pages
1609–1618
Identifiers
PMID: 16529733
Source
Medline
License
Unknown

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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