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

Emanuele Attolino; Ian Cumpstey; Antony J Fairbanks

doi:10.1016/j.carres.2006.02.022

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

Carbohydr Res. 2006 Jul 24;341(10):1609-18. doi: 10.1016/j.carres.2006.02.022. Epub 2006 Mar 10.

Authors

Emanuele Attolino¹, Ian Cumpstey, Antony J Fairbanks

Affiliation

¹ Chemistry Research Laboratory, Oxford University, Mansfield Road, Oxford OX1 3TA, UK.

PMID: 16529733
DOI: 10.1016/j.carres.2006.02.022

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Allyl Compounds / chemistry
Glycosylation
Oligosaccharides / chemical synthesis*

Substances

Allyl Compounds
Oligosaccharides
methyl glucopyranosyl-1-2-glycopyranosyl-1-3-glucopyranosyl-1-3-mannopyranoside