Clinical analysis on steroids. XII. Occurrence of D-homoannulation during the hot acid hydrolysis of 5 beta-pregnane-3 alpha, 20 alpha-diol disulfate.
Two D-homosteroids were isolated from the hydrolyzate of 5 beta-pregnane -3 alpha, 20 alpha-diol disulfate (II) when it was refluxed in 3N hydrochloric acid. The structures of these steroids have been elucidated as 17 alpha-methyl-D-homo-5 beta-androstane-3 alpha, 17a beta-diol (VI) and 17 alpha-methyl-17a beta-chloro-D-homo-5 beta-androstan-3 alpha-ol (VIII) by instrumental analyses. The former was identical with a synthetic specimen derived from 5 beta-pregnane-3 alpha, 20 beta-diol disulfate (IV) by uranediol rearrangement. The main hydrolyzates obtained were 17 alpha-ethyl-17 beta-methyl-18-nor-5 beta-androst-13-en-3 alpha-ol (V) and 5 beta-pregnane-3 alpha, 20 alpha-diol (III).
D015113:Androstane-3,17-diol / Q000031:analogs & derivatives; D000732:Androstanols; D002845:Chromatography; D006718:Homosteroids; D006868:Hydrolysis; D011276:Pregnanediol
D000732:Androstanols; D006718:Homosteroids; D015113:Androstane-3,17-diol; C016836:allopregnane-3,20-diol; C026421:17-methyl-17a-chloro-D-homoandrostan-3-ol; C026419:17-methyl-D-homoandrostane-3,17-diol; D011276:Pregnanediol