Ready access to a branched Man5 oligosaccharide based on regioselective glycosylations of a mannose-tetraol with n-pentenyl orthoesters

Clara Uriel; Ana M Gómez; J Cristóbal López; Bert Fraser-Reid

doi:10.1039/c2ob26432c

Ready access to a branched Man5 oligosaccharide based on regioselective glycosylations of a mannose-tetraol with n-pentenyl orthoesters

Org Biomol Chem. 2012 Oct 3;10(41):8361-70. doi: 10.1039/c2ob26432c.

Authors

Clara Uriel¹, Ana M Gómez, J Cristóbal López, Bert Fraser-Reid

Affiliation

¹ Instituto de Química Orgánica General, Madrid, Spain.

PMID: 23001311
DOI: 10.1039/c2ob26432c

Abstract

A branched Man(5) oligosaccharide has been synthesized by sequential regioselective glycosylations on a mannose-tetraol with n-pentenyl orthoester glycosyl-donors promoted by NIS/BF(3)·Et(2)O, in CH(2)Cl(2). An extended n-pentenyl chain was incorporated into the tetraol acceptor to facilitate (a) the solubility of the starting tetraol in CH(2)Cl(2), and (b) future manipulations at the reducing end of the Man(5) oligosaccharide.

Publication types

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

MeSH terms

Carbohydrate Sequence
Esters / chemistry*
Glycosylation
Mannans / chemistry*
Mannose / chemistry*
Molecular Sequence Data
Oligosaccharides / chemistry*
Stereoisomerism

Substances

Esters
Mannans
Oligosaccharides
mannosyl(9)-N-acetylglucosamine
Mannose