Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors

Jeroen D C Codée; Leendert J van den Bos; Remy E J N Litjens; Herman S Overkleeft; Jacques H van Boom; Gijs A van der Marel

doi:10.1021/ol034528v

Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors

Org Lett. 2003 May 29;5(11):1947-50. doi: 10.1021/ol034528v.

Authors

Jeroen D C Codée¹, Leendert J van den Bos, Remy E J N Litjens, Herman S Overkleeft, Jacques H van Boom, Gijs A van der Marel

Affiliation

¹ Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.

PMID: 12762693
DOI: 10.1021/ol034528v

Abstract

[reaction: see text] A novel sequential glycosylation procedure is described that combines the use of 1-hydroxyl and thiodonors. The Ph(2)SO/Tf(2)O-mediated dehydrative condensation of 1-hydroxyl donors with thioglycosides affords in good yield the thiodisaccharides, which in turn can be activated by the same activator system to furnish trisaccharides. The alpha-Gal epitope and a hyaluronan trisaccharide were efficiently assembled in a one-pot procedure.

Publication types

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

MeSH terms

Carbohydrate Sequence
Glycosylation*
Indicators and Reagents
Molecular Sequence Data
Trisaccharides / chemical synthesis*

Substances

Indicators and Reagents
Trisaccharides