A Chemo-Enzymatic Synthesis of D-Allosamine Derivatives from Tri-O-acetyl- D-glucal

Takeshi Sugai, Hanako Okazaki, Atsuhito Kuboki, Hiromichi Ohta

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Abstract

N-Acetyl-D-allosamine and its derivatives were synthesized from tri-O-acetyl-D-glucal based on lipase-catalyzed selective protection of primary alcohols, [3,3] sigmatropic rearrangement of allylic trichloroacetimidates, and stereo- selective ruthenium-catalyzed dihydroxylation. In the course of this study, it was revealed that the Pseudomonas lipase- catalyzed acetylation occurred in a high yield (> 90%) exclusively at the primary alcohols of three Ferrier rearrangement products derived from tri-O-acetyl-D-glucal.

Original languageEnglish
Pages (from-to)2535-2540
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume70
Issue number10
DOIs
Publication statusPublished - 1997 Oct

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ASJC Scopus subject areas

  • Chemistry(all)

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