A simple preparation of 2,3,4,6-tetra-o-acyl-gluco-, galacto- and mannopyranoses and relevant theoretical study.
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.
Wang
Zerong Daniel
ZD
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
Mo
Yirong
Y
Chiou
Chiao-Lun
CL
Liu
Minghong
M
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
D005947:Glucose; D008358:Mannose; D005690:Galactose