“糖螺旋甾烷”的合成——具有类糖环F的甾体皂苷元。
Synthesis of "glycospirostanes"--steroid sapogenins with a sugar-like ring F.
作者信息
López Yliana, Jastrzebska Izabella, Santillan Rosa, Morzycki Jacek W
机构信息
Institute of Chemistry, University of Białystok, Piłsudskiego 11/4, 15-443 Białystok, Poland.
出版信息
Steroids. 2008 Apr;73(4):449-57. doi: 10.1016/j.steroids.2007.12.015. Epub 2008 Feb 19.
The synthesis of two "glycospirostanes" from 23-oxotigogenin acetate is described. (23S,24S,25R)-5alpha-Spirostane-3beta,23,24,25-tetraol was obtained by dehydrogenation followed by stereoselective reduction of the 23-oxo group and OsO(4) dihydroxylation of the C24-C25 double bond. Allylic hydroxylation with SeO(2) of 3beta-acetoxy-5alpha-spirost-23-ene obtained from 23-oxotigogenin acetate followed by OsO(4) dihydroxylation of the C23-C24 double bond afforded (23R,24S,25R)-5alpha-spirostane-3beta,23,24,25-tetraol.
描述了由醋酸23 - 氧代替告皂苷元合成两种“糖螺甾烷”的过程。通过脱氢，随后对23 - 氧代基团进行立体选择性还原以及对C24 - C25双键进行锇酸（OsO₄）二羟基化反应，得到了(23S,24S,25R)-5α - 螺甾烷 - 3β,23,24,25 - 四醇。由醋酸23 - 氧代替告皂苷元得到的3β - 乙酰氧基 - 5α - 螺甾 - 23 - 烯经二氧化硒（SeO₂）进行烯丙基羟基化反应，随后对C23 - C24双键进行锇酸（OsO₄）二羟基化反应，得到了(23R,24S,25R)-5α - 螺甾烷 - 3β,23,24,25 - 四醇。
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