Glycosylation of l,4:3,6-dianhydro-D-glucitol (isosorbide)

David J Claffey; Mary F Casey; Patrick A Finan

doi:10.1016/j.carres.2004.07.007

Glycosylation of l,4:3,6-dianhydro-D-glucitol (isosorbide)

Carbohydr Res. 2004 Oct 4;339(14):2433-40. doi: 10.1016/j.carres.2004.07.007.

Authors

David J Claffey¹, Mary F Casey, Patrick A Finan

Affiliation

¹ Chemistry Department, National University of Ireland, Galway, Ireland.

PMID: 15388358
DOI: 10.1016/j.carres.2004.07.007

Abstract

Condensation of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-, 2,3,4-tri-O-acetyl-alpha-D-xylopyranosyl- and of 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromides with l,4:3,6-dianhydro-D-glucitol under Koenigs-Knorr conditions, and using the Helferich modification of the reaction showed regioselectivity in glysosylation at C-5 of isosorbide.

MeSH terms

Bromides / chemistry
Glycosides / chemistry*
Glycosylation
Isosorbide / chemistry*
Molecular Structure
Monosaccharides / chemistry

Substances

Bromides
Glycosides
Monosaccharides
Isosorbide