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InChI:InChI=1/C21H35ClO/c1-13-4-7-17-16-6-5-14-12-15(23)8-10-20(14,2)18(16)9-11-21(17,3)19(13)22/h13-19,23H,4-12H2,1-3H3/t13-,14-,15-,16+,17+,18+,19+,20+,21+/m1/s1

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• 68157-67-5 5β-pregnane-3α,20α-diol disulfate dipotassium salt 

Relevant academic research and scientific papers

Mechanism of the D-Homoannulation of Pregnanediol Disulfate in Refluxing 3 N Hydrochloric acid

In order to elucidate the mechanism of D-homoannulation of pregnanediol 20-sulfate, solvolysis of -5β-pregnane-3α,20α-diol disulfate (3) in refluxing 3 N hydrochloric acid was investigated.The resulting D-homosteroids, 17percenta-methyl-D-homo-5β-androstane-3α,17aβ-diol (8) and 17α-methyl-17aβ-chloro-D-homo-5β-androstan-3α-ol (10), contained a quantitative amount of (13)C only at C-17, indicating that the ring-enlargement reaction of the 20α-ol sulfate proceeded with stereospecific migration of the C16-C17 bond.The same result was obtained from isomeric -5β-pregnane-3α,20β-diol disulfate (6).Based on these results,the D-homoannulation of pregnanediol 20-sulfate was concluded to proceed by a stepwise mechanism through the C-20 carbocation.The stereochemistry of this Wagner-Meerwein type rearrangement reaction is also discussed. Keywords --- 5β-pregnane-3α,20α-diol (pregnanediol); pregnanediol disulfate; 5β-pregnane-3α,20β-diol; D-homoannulation; stereochemistry; steroidal sulfate; acid hydrolysis; (13)C-NMR

Clinical Analysis on Steroids. XII. Occurrence of D-Homoannulation during the Hot Acid Hydrolysis of 5β-Pregnane-3α,20α-diol Disulfate

Two D-homosteroids were isolated from the hydrolyzate of 5β-pregnane-3α,20α-diol disulfate (II) when it was refluxed in 3N hydrochloric acid.The structures of these steroids have been elucidated as 17α-methyl-D-homo-5β-androstane-3α,17aβ-diol (VI) and 17α-methyl-17aβ-chloro-D-homo-5β-androstan-3α-ol (VIII) by instrumental analyses.The former was identical with a synthetic specimen derived from 5β-pregnane-3α,20β-diol disulfate (IV) by uranediol rearrangement.The main hydrolyzates obtained were 17α-ethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol (V) and 5β-pregnane-3α-20α-diol (III).