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

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

1
Department of Chemistry, School of Science and Computer Engineering, University of Houston-Clear Lake, 2700 Bay Area Boulevard, Houston, TX 77058, USA
2
Department of Chemistry, Western Michigan University, Kalamazuo, MI 49008, USA
3
Department of Chemical & Biomolecular Engineering, University of Houston, Houston, TX 77204-4004, USA
4
Chemistry Department, University of North Carolina-Charlotte, Charlotte, NC 28223, USA
*
Authors to whom correspondence should be addressed.
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
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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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