化学学报 ›› 2001, Vol. 59 ›› Issue (10): 1653-1659. 上一篇    下一篇

研究论文

皂素皂苷脂肪链中甲基绝对构型的确定

朱向明;曾文彬;俞飚;惠永正   

  1. 中国科学院上海有机化学研究所.上海(200032);中国科学院生命有机化学国家 重点实验室
  • 发布日期:2001-10-15

Determination of the absolute configuration of methyl group in the acyl moiety of quillajasaponins

Zhu Xiangming;Zeng Wenbin;Yu Bian;Hui Yongzheng   

  1. Shanghai Inst Organ Chem., CAS.Shanghai(200032)
  • Published:2001-10-15

利用Sharpless环氧化和Roush反应合成了皂素苷脂肪链中C9脂肪酸单体的两个非对映异构体,即(3S,5S,6S)-3,5-二羟基-6-甲基-δ-辛酸内酯和(3S,5S,6R)-3,5-二羟基-6-甲基-δ-辛酸内酯。通过与天然样品进行理化数据对比,确定了皂素皂苷脂肪链中甲基的绝对构型为S。

关键词: 皂素皂苷, 脂肪酸, 构型, 环氧化反应, 辛酸内酯

Two diastereoisomers of the C9 lactone, (3S, 5S, 6S) -3,5- dihydroxy- 6-methyl-δ-octanolide and (3S, 5S, 6S)-3,5-dihydroxy-6- methyl-δ- octanolide, have been enantioselectively synthesized and compared with the natural sample, thereby determining the absolute configuration of the methyl group in the acyl moiety of quillajasaponins to be S.

Key words: FATTY ACID, CONFIGURATION, EPOXIDATION REACTION

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