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

T Sugai, H Okazaki, A Kuboki, H Ohta

文献索引：Sugai, Takeshi; Okazaki, Hanako; Kuboki, Atsuhito; Ohta, Hiromichi Bulletin of the Chemical Society of Japan, 1997 , vol. 70, # 10 p. 2535 - 2540

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被引用次数: 13

摘要

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 stereoselective 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 ...