Work

A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study

Year: 2010

Type: article

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.

Source: Molecules

DOI: 10.3390/molecules15010374

Authors: Zerong Daniel Wang, Yirong Mo, Chiao-Lun Chiou, Minghong Liu

Institutions: University of Houston - Clear Lake, Western Michigan University, University of Houston, University of North Carolina at Charlotte

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,258

Funders: Welch Foundation, University of Houston