化学学报 ›› 1962, Vol. 28 ›› Issue (4): 204-211. 上一篇    下一篇

论文

植物甾醇C24的绝对构型

黄維垣, 徐锦文   

  1. 中国科学院有机化学研究所
  • 投稿日期:1961-09-28 发布日期:2013-06-03

THE ABSOLUTE CONFIGURATION AT C24 OF PHYTOSTEROLS

HUANG WEI-YUAN, HSU JIN-WEN   

  1. Institute of Organic Chemistry, Academia Sinica
  • Received:1961-09-28 Published:2013-06-03

自然界中存在一系列的甾醇类化合物, 在C24上具取代基, 例如麦角甾醇(ergosterol, Ⅰ)及菜子甾醇(campesterol, Ⅱ)等为甲基衍生物;大豆甾醇(stigmasterol, Ⅲ)、β-麦胚甾醇(β-sitoscefol, Ⅳ)及γ-麦胚甾醇(γ-sitosterol, Ⅴ)等为乙基衍生物, 因而形成一不对称碳中心.由于该碳原子与分子中的其他不对称碳原子距离较远, 因此在构型上不易与后者相互联系, 所以C24的相对和绝对构型的测定乃成为独立的研究裸题.

The absolute configuration at G4 of phytosterols was established by chemical method, namely:(+)-limonene with known absolute configuration was degraded through a series of steps to S(-)-5-ethyl-6-methylheptanone-2 and S(-)-5, 6 dimethylheptanone-2, which were identical with the compounds obtained from the side chain oxidative degradation of y-sitosterol and ergosterol respectively.Thus the 24刀configuration of the above mentinned sterols was established.