Glycosyl hydroperoxides derived from 2-deoxysugars

Barbara Szechner; Zofia Urbańczyk-Lipkowska; Marek Chmielewski

doi:10.1016/j.carres.2010.09.005

Glycosyl hydroperoxides derived from 2-deoxysugars

Carbohydr Res. 2010 Nov 22;345(17):2464-8. doi: 10.1016/j.carres.2010.09.005. Epub 2010 Sep 7.

Authors

Barbara Szechner¹, Zofia Urbańczyk-Lipkowska, Marek Chmielewski

Affiliation

¹ Institute of Organic Chemistry of Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

PMID: 20933224
DOI: 10.1016/j.carres.2010.09.005

Abstract

Oxidation of 3,4,6-tri-O-benzyl-2-deoxy-d-glucose and d-galactose or their t-butyl glycosides to the corresponding glycosyl hydroperoxides can be performed with hydrogen peroxide in the presence of an acid catalyst. Several reaction conditions and their influence on the effectiveness of the oxidation are discussed. Separation of the α - and β-anomers of the glycosyl hydroperoxides was achieved through mixed peroxide formation by reaction of the hydroperoxide group with 2-methoxypropene and subsequent deprotection.

Publication types

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

MeSH terms

Carbohydrate Conformation
Deoxy Sugars / chemistry*
Glycosides / chemistry*
Hydrogen Peroxide / chemistry*
Models, Molecular
Quantum Theory

Substances

Deoxy Sugars
Glycosides
Hydrogen Peroxide