化学
非对映体
硼氢化
单糖
衍生工具(金融)
溴化物
糖苷
醛糖
格氏反应
葡萄糖苷
苷元
有机化学
立体化学
试剂
催化作用
经济
替代医学
病理
金融经济学
医学
作者
Shigeru Kobayashi,Jun Furukawa,Tomoko Sakai,Nobuo Sakairi
标识
DOI:10.1016/s0008-6215(02)00092-7
摘要
The 6-O-mesyl derivative of phenyl 1-thio-beta-D-glucopyranoside was prepared from D-glucose as a synthetic equivalent of a 6-deoxy-hexosyl donor. Racemic methyl 11-hydroxytetradecanoate (methyl convolvulinolate) was synthesized by Grignard reaction of propylmagnesium bromide with 10-undecenal followed by hydroboration. Both intermediates were coupled by NIS-TfOH-promoted glycosidation to give a mixture of two diasteromeric glucopyranosides, which were separated on a preparative scale by medium pressure chromatography. One of the products was identified as having the natural (S)-configuration by comparison of its 1H NMR spectrum with an authentic sample prepared from the corresponding chiral hydroxyfatty acid.
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