SYNTHESIS OF THE SULFATES DERIVED FROM 5-ALPHA-CHOLESTANE-3-BETA,6-ALPHA-DIOL

Three new steroid sulfates-3-beta-hydroxy-5-alpha-cholestan-6-alpha-yl sulfate, 6-alpha-hydroxy-5-alpha-cholestan-3-beta-yl sulfate, and 5-alpha-cholestan-3-beta,6-alpha-diyl disulfate-were synthesized. For the syntheses of the key intermediates, 3-beta-hydroxy-5-alpha-cholestan-6-alpha-yl acetate a...

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Bibliographic Details
Published inSteroids Vol. 57; no. 5; pp. 233 - 235
Main Authors ARNOSTOVA, LM, POUZAR, DRASAR, P
Format Journal Article
LanguageEnglish
Published NEW YORK Elsevier 01.05.1992
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Summary:Three new steroid sulfates-3-beta-hydroxy-5-alpha-cholestan-6-alpha-yl sulfate, 6-alpha-hydroxy-5-alpha-cholestan-3-beta-yl sulfate, and 5-alpha-cholestan-3-beta,6-alpha-diyl disulfate-were synthesized. For the syntheses of the key intermediates, 3-beta-hydroxy-5-alpha-cholestan-6-alpha-yl acetate and 6-alpha-hydroxy-5-alpha-cholestan-3-beta-yl acetate, selective protection of hydroxy groups in 5-alpha-cholestane-3-beta,6-alpha-diol was necessary. This problem was solved by using a combination of acetyl, tetrahydropyranyl, and methoxymethyl protective groups, which represents a new approach leading to these hydroxy acetates. Sulfated derivatives of 5-alpha-cholestane-3-beta,6-alpha-diol are present in marine invertebrates and were synthesized for the purposes of biologic testing.
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ISSN:0039-128X
1878-5867
DOI:10.1016/0039-128X(92)90107-K