title: A simple preparation of 2,3,4,6-tetra-o-acyl-gluco-, galacto- and mannopyranoses and relevant theoretical study.
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.
authors.affiliation: 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
authors.forename: Zerong Daniel
authors.initials: ZD
authors.lastname: Wang
authors.forename: Yirong
authors.initials: Y
authors.lastname: Mo
authors.forename: Chiao-Lun
authors.initials: CL
authors.lastname: Chiou
authors.forename: Minghong
authors.initials: M
authors.lastname: Liu
mesh_terms: D002236:Carbohydrate Conformation; D005690:Galactose / Q000138:chemical synthesis* / Q000737:chemistry; D005947:Glucose / Q000138:chemical synthesis* / Q000737:chemistry; D008358:Mannose / Q000138:chemical synthesis* / Q000737:chemistry; D013816:Thermodynamics
chemical_list: D005947:Glucose; D008358:Mannose; D005690:Galactose