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.
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.
Lu
Wallach
W
Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1.
Navidpour
Latifeh
L
Taylor
Scott D
SD
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
D005960:Glucosides; D008362:Mannosides; C503494:benzyl 2,3,4-tri-O-benzylglucopyranoside; C503495:benzyl 2,3,4-tri-O-benzylmannopyranoside; D005947:Glucose; D008358:Mannose