Efficient Large Scale Syntheses of 3-Deoxy-D-manno-2-octulosonic acid (Kdo) and Its Derivatives.
作者： Yingle Feng , Jie Dong , Fangyuan Xu , Aiyun Liu , Li Wang
DOI: 10.1021/ACS.ORGLETT.5B00901
关键词: Organic chemistry 、 2-Octulosonic acid 、 Ethyl ester 、 Stereochemistry 、 Epimer 、 Glycal 、 Yield (chemistry) 、 Chemistry 、 Stereoselectivity
摘要: An efficient method to rapidly synthesize 3-deoxy-d-manno-2-octulosonic acid (Kdo) and its derivatives in large scale has been developed. Starting from d-mannose, the di-O-isopropylidene derivative of Kdo ethyl ester was prepared three steps on a more than 40 g one batch an overall yield 75–80% without any intermediate purification. Kdo, glycal, 2-acetylated were synthesized quickly high ester. 2-Deoxy-β-Kdo obtained with stereoselectivity via epimerization α-isomer using t-BuOH as proton source.
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