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 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.
Arnostová
L M
LM
Institute of Organic Chemistry and Biochemistry, Prague, Czechoslovakia.
Pouzar
V
V
Drasar
P
P
D002776:Cholestanes / Q000138:chemical synthesis*; D002777:Cholestanols / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013431:Sulfates / Q000138:chemical synthesis*; D013464:Sulfuric Acids / Q000138:chemical synthesis / Q000737:chemistry
D002776:Cholestanes; D002777:Cholestanols; D013431:Sulfates; D013464:Sulfuric Acids; C076664:cholestan-3,6-diyl disulfate; C076666:6-hydroxycholestan-3-yl sulfate; C076667:3-hydroxycholestan-6-yl sulfate