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

• Published in: Steroids Vol. 57; no. 5; pp. 233 - 235
• Main Authors: ARNOSTOVA, LM, POUZAR, DRASAR, P
• Format: Journal Article
• Language: English
• Published: NEW YORK Elsevier 01.05.1992
• Subjects: Biochemistry & Molecular Biology; Cholestanes - chemical synthesis; Cholestanols - chemical synthesis; Cholestanols - chemistry; Endocrinology & Metabolism; Life Sciences & Biomedicine; Molecular Structure; Science & Technology; Sulfates - chemical synthesis; Sulfuric Acids - chemical synthesis; Sulfuric Acids - chemistry; PROTECTIVE GROUPS; STEROIDS; STEROID HYDROXY SULFATES; MARINE INVERTEBRATES; SYNTHESIS; 5-ALPHA-CHOLESTANE-3-BETA,6-ALPHA-DIOL; SELECTIVE PROTECTION OF STEROID DIOLS
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/0039-128X(92)90107-K

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.