由肌醇实际合成所有肌醇立体异构体。

Practical synthesis of all inositol stereoisomers from myo-inositol.

作者信息

Chung S K, Kwon Y U

机构信息

Department of Chemistry, Pohang University of Science & Technology, Korea.

出版信息

Bioorg Med Chem Lett. 1999 Aug 2;9(15):2135-40. doi: 10.1016/s0960-894x(99)00348-0.

DOI:10.1016/s0960-894x(99)00348-0

PMID:10465532

Abstract

Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis-inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.

摘要

通过由肌醇制备的conduritol中间体成功合成了六种肌醇立体异构体。对conduritol B、C和F衍生物进行二羟基化和环氧化，然后开环，得到表肌醇、别肌醇、粘质肌醇、新肌醇、DL-手性肌醇和鲨肌醇。不能通过这种方法制备的顺式肌醇衍生物，以2-O-苯甲酰基-肌醇原甲酸酯为关键中间体，经5步合成。