Stereoselectivity of Reactions at the Glycoside Center of Carbohydrates: VII. Synthesis of Aryl α-and-β-D-Glucopyranosides by Helferich, Catalyzed by Boron …

VM Sokolov, VI Zakharov, EP Studentsov

Index: Sokolov; Zakharov; Studentsov Russian Journal of General Chemistry, 2002 , vol. 72, # 5 p. 806 - 811

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Citation Number: 20

Abstract

Abstract 13 C NMR spectroscopy was used to study the stereoselectivity of glycosylation of phenols with the α and β anomers of penta-O-acetyl-D-glucopyranose, penta-O- trifluoroacetyl-D-glucopyranose, and 2, 3, 4, 6-tetra-O-acetyl-1-O-trifluoroacetyl-D- glucopyranose in the presence of boron trifluoride etherate at varied temperature, time, and catalyst amount. The boron trifluoride etherate-catalyzed reaction of penta-O-acetyl-β-D- ...