A simple preparation of 2,3,4,6-tetra-o-acyl-gluco-, galacto- and mannopyranoses and relevant theoretical study

Zerong Daniel Wang; Yirong Mo; Chiao-Lun Chiou; Minghong Liu

doi:10.3390/molecules15010374

A simple preparation of 2,3,4,6-tetra-o-acyl-gluco-, galacto- and mannopyranoses and relevant theoretical study

Molecules. 2010 Jan 18;15(1):374-84. doi: 10.3390/molecules15010374.

Authors

Zerong Daniel Wang¹, Yirong Mo, Chiao-Lun Chiou, Minghong Liu

Affiliation

¹ Department of Chemistry, School of Science and Computer Engineering, University of Houston-Clear Lake, 2700 Bay Area Boulevard, Houston, TX 77058, USA. wang@uhcl.edu

Abstract

The deacylation of glucose, galactose and mannose pentaacetates, galactose and mannose penta(3-bromo)benzoates, as well as the dealkylation of 2,3,4,6-tetra-O-acetyl and 2,3,4,6-tetra-O-(3-bromo)benzoyl methyl alpha-D-glucopyranosides have been studied. In addition, a computational study on the deacylation of beta-D-glucose pentaacetate has been carried out with density functional theory (B3LYP/6-31G*). The anomeric effect during deacetylation and dealkylation has been clearly demonstrated in both experimental and computational results.

Publication types

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

MeSH terms

Carbohydrate Conformation
Galactose / chemical synthesis*
Galactose / chemistry
Glucose / chemical synthesis*
Glucose / chemistry
Mannose / chemical synthesis*
Mannose / chemistry
Thermodynamics

Substances

Glucose
Mannose
Galactose