A Chemo-Enzymatic Synthesis of D-Allosamine Derivatives from Tri-O-acetyl-D-glucal
A Chemo-Enzymatic Synthesis of D-Allosamine Derivatives from Tri-O-acetyl-D-glucal
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三-O-乙酰-D-葡萄糖化学酶法合成D-别糖胺衍生物
DOI：
10.1246/bcsj.70.2535
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发表时间：
1997
影响因子：
4
通讯作者：
H. Ohta
中科院分区：
文献类型：
--
作者：
T. Sugai;Hanako Okazaki;A. Kuboki;H. Ohta
以脂肪酶催化伯醇的选择性保护、烯丙基三氯乙酰亚甲酸酯的[3，3]S型重排和Ru催化的立体选择性二羟化反应为基础，合成了N-乙酰基-D-异构胺及其衍生物。在本研究过程中，发现假单胞菌脂肪酶催化的乙酰化反应仅在三个由三-O-乙酰基-D-葡萄糖醛衍生的费里尔重排产物的伯醇上发生，产率高达90%。
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 rearrangement products derived from tri-O-acetyl-D-glucal.