title: An expedient synthesis of benzyl 2,3,4-tri-O-benzyl-beta-D-glucopyranoside and benzyl 2,3,4-tri-O-benzyl-beta-D-mannopyranoside.
abstract: An efficient three-step synthesis of benzyl 2,3,4-tri-O-benzyl-beta-D-glucopyranoside, a widely used building block in carbohydrate chemistry, is described. The key step is the selective debenzylation-acetylation of perbenzylated beta-glucose using ZnCl2-Ac2O-HOAc. This approach was also used to affect an efficient three-step synthesis of benzyl 2,3,4-tri-O-benzyl-beta-D-mannopyranoside.
authors.affiliation: Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1.
authors.forename: Wallach
authors.initials: W
authors.lastname: Lu
authors.forename: Latifeh
authors.initials: L
authors.lastname: Navidpour
authors.forename: Scott D
authors.initials: SD
authors.lastname: Taylor
mesh_terms: D005947:Glucose / Q000138:chemical synthesis* / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D008358:Mannose / Q000138:chemical synthesis* / Q000737:chemistry; D008362:Mannosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D005960:Glucosides; D008362:Mannosides; C503494:benzyl 2,3,4-tri-O-benzylglucopyranoside; C503495:benzyl 2,3,4-tri-O-benzylmannopyranoside; D005947:Glucose; D008358:Mannose