Synthesis of polyhydroxy ocean steroid (25R)-5 alpha-cholesteric-2 beta,3 alpha,26-triol

A synthetic method and polyhydric technology, applied in the direction of steroids, organic chemistry, etc., can solve the problem of low content and achieve a scientific and reasonable synthetic route
CN101220073AInactive Publication Date: 2008-07-16SUN YAT SEN UNIV
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
SUN YAT SEN UNIV
Publication Date
2008-07-16
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention discloses a synthetic method of a polyhydroxy marine steroid (25R)-5 Alpha- cholest-2 Beta and a 3 Alpha and 26-triol, which uses a low-cost Tigogenin as the raw material and obtains (25R)-5 Alpha-cholest-2-ene-16 Beta and 26-diol through the TsCl esterification, elimination reaction and the reduction of zinc powder / ethanol system, obtains (25R)-26-O- t butyl dimethysilyl-5 Alpha- cholest-2-ene through selectively protecting C-26- hydroxyl, C-16-hydroxyl ethlsulphonic acid esterification and lithium aluminum hydride reduction by t-butyl dimethylsilyl chloride, and at last gets the object compound (25R)-5 Alpha- cholest-2 Beta, 3 Alpha and 26-triol through ring-opening under the acid conditions after the epoxidation. The synthetic route of the invention is characterized in that: the synthetic raw material is of low-cost and easy to get; the synthetic route is scientific and reasonable, etc. The target compound has potential antitumor and antivirus activity.
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Description

Technical field

[0001] The invention relates to a method for synthesizing polyhydroxy marine steroids. Background technique

[0002] Marine organisms have developed their unique metabolic methods under their special environment, which contains a large number of substances with peculiar structure, strong physiological activity and special effects. Marine sterols are an important part of biofilms and the precursors of certain hormones. They have strong biological activity. (25R)-5α-cholesterol-2β, 3α, 26-triol is derived from marine organisms (Ophiarachna incrassara) A polyhydroxy marine steroid compound (M. Valeria D'Auria, J. Org. Chem, 1987, 52(18), 3947-3952) found in The 2β, 3α hydroxyl group has a unique 26-hydroxyl group on the 17-position side chain.

[0003]

[0004] The compound and its derivatives are expected to be further studied in such aspects as antitumor, antiviral, hypolipidemic, neuroprotection, etc. (XIONG Fu, Journal of Natnral Products, 1994, 57, (11), 1591-...

Claims

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