Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
α-D-Glucosylation by 6-O-Acetyl-2,3,4-tri-O-benzyl-D-glucopyranose Using Trimethylsilyl Triflate and Pyridine. Synthesis of α-Maltosyl and α-Isomaltosyl α-D-Glucosides
Shinkiti KotoKazuo YagoShonosuke ZenFumiya TomonagaShigehiko Shimada
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1986 Volume 59 Issue 2 Pages 411-414

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Abstract

The D-glucosylation of methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside and methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside by 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose using pyridine and excess trimethylsilyl triflate was carried out in dichloromethane, 1,2-dimethoxyethane, and acetonitrile. In a given solvent, the selectivity of the reaction varied depending on the type of hydroxyl group of the glucosyl acceptors. The D-glucosylation of these acceptors with 6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose employing this reagent system in dichloromethane proceeded with good α-selectivity irrespective of the type of the hydroxyl group. This α-D-glucosylation was applied for the synthesis of O-α-D-glucopyranosyl-(1→4)- and -(1→6)-α-D-glucopyranosyl α-D-glucopyranosides from α,α-trehalose.

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