（±）-1,5,6-三-O-苄基-myo-肌醇的合成与拆分

The synthesis and resolution of (+/-)-1,5,6-tri-O-benzyl-myo-inositol.

作者信息

Desai T, Fernandez-Mayoralas A, Gigg J, Gigg R, Payne S

机构信息

Laboratory of Lipid and General Chemistry, National Institute for Medical Research, London, Great Britain.

出版信息

Carbohydr Res. 1990 Sep 19;205:105-23. doi: 10.1016/0008-6215(90)80132-m.

DOI:10.1016/0008-6215(90)80132-m

PMID:2276129

Abstract

Racemic 1,5,6-tri-O-benzyl-myo-inositol was prepared by five routes and converted into 1,5,6-tri-O-benzyl-2,3-O-isopropylidene-myo-inositol, the camphanates of which were readily separated by chromatography. The absolute configurations of the chiral derivatives were established by their conversion into the known chiral 1,4,5,6-tetra-O-benzyl-myo-inositols. 1D-1,5,6-Tri-O-benzyl-2,3-O-isopropylidene-myo-inositol was converted into 1D-1,3,5,6-tetra-O-benzyl-myo-inositol and thence into 1D-2,4-di-O-methyl-myo-inositol. 1D-1,5,6-Tri-O-benzyl-myo-inositol was converted into 1D-1,2,5,6-tetra-O-benzyl-myo-inositol, the diacetate of which is a chiral analogue of "thermosalient crystals". The potential of the above compounds for the synthesis of natural products is surveyed.

摘要

通过五条路线制备了外消旋1,5,6-三-O-苄基-myo-肌醇，并将其转化为1,5,6-三-O-苄基-2,3-O-异亚丙基-myo-肌醇，其樟脑酸酯可通过色谱法轻松分离。通过将手性衍生物转化为已知的手性1,4,5,6-四-O-苄基-myo-肌醇来确定其绝对构型。1D-1,5,6-三-O-苄基-2,3-O-异亚丙基-myo-肌醇被转化为1D-1,3,5,6-四-O-苄基-myo-肌醇，进而转化为1D-2,4-二-O-甲基-myo-肌醇。1D-1,5,6-三-O-苄基-myo-肌醇被转化为1D-1,2,5,6-四-O-苄基-myo-肌醇，其二乙酸酯是“热致突出晶体”的手性类似物。考察了上述化合物在天然产物合成中的潜力。