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Molecules 2010, 15(1), 374-384; doi:10.3390/molecules15010374
Article

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

1,* , 2,* , 1,3 and 2,4
Received: 12 November 2009 / Revised: 16 December 2009 / Accepted: 22 December 2009 / Published: 18 January 2010
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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 α-D-glucopyranosides have been studied. In addition, a computational study on the deacylation of β-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.
Keywords: deacetylation; dealkylation; anomeric effect; deacylation; density functional theory deacetylation; dealkylation; anomeric effect; deacylation; density functional theory
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Wang, Z.D.; Mo, Y.; Chiou, C.-L.; Liu, M. A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study. Molecules 2010, 15, 374-384.

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