.ALPHA.-D-glucosylation by 6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose using trimethylsilyl triflate and pyridine. Synthesis of .ALPHA.-maltosyl and .ALPHA.-isomaltosyl .ALPHA.-D-glucosides.

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概要

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• The D-glucosylation of methyl 2,3,4-tri-<I>O</I>-benzyl-α-D-glucopyranoside and methyl 2,3,6-tri-<I>O</I>-benzyl-β-D-glucopyranoside by 2,3,4,6-tetra-<I>O</I>-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-<I>O</I>-acetyl-2,3,4-tri-<I>O</I>-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 <I>O</I>-α-D-glucopyranosyl-(1→4)- and -(1→6)-α-D-glucopyranosyl α-D-glucopyranosides from α,α-trehalose.

• 公益社団法人 日本化学会の論文

著者

• TOMONAGA Fumiya

  Department of Pharmacy, Kitasato University Hospital

• Yago Kazuo

  Department Of Hospital Pharmacy Kitasato University East Hospital

• Zen Shonosuke

  School Of Pharmaceutical Sciences Kitasato University

• Koto Shinkiti

  School Of Pharmaceutical Sciences Kitasato University

• Shimada Shigehiko

  Department Of Hospital Pharmacy Kitasato University Hospital

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