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

被引：14

作者：

ARNOSTOVA, LM ^{[1
]}

POUZAR, V ^{[1
]}

DRASAR, P ^{[1
]}

机构：

[1] CZECHOSLOVAK ACAD SCI, INST ORGAN CHEM & BIOCHEM, CS-16610 PRAGUE 6, CZECHOSLOVAKIA

来源：

STEROIDS | 1992年 / 57卷 / 05期

关键词：

STEROIDS; 5-ALPHA-CHOLESTANE-3-BETA; 6-ALPHA-DIOL; STEROID HYDROXY SULFATES; MARINE INVERTEBRATES; SYNTHESIS; PROTECTIVE GROUPS; SELECTIVE PROTECTION OF STEROID DIOLS;

D O I：

10.1016/0039-128X(92)90107-K

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：233 / 235

页数：3

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