A facile synthesis of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol.

Abstract:

:A convenient procedure for the synthesis of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol via a modified homologation sequence of the intermediate 3 alpha,7 alpha,12 alpha-triformyloxy-24-oxo-25-diazo-25-homo-5 beta-cholane involving a homogeneous medium is described. This involves treating the intermediate alpha-diazoketone in methanol with a solution of silver benzoate in triethylamine. Grignard reaction of the resulting triformyloxy methyl homocholate yielded 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol. Large amounts of this bile alcohol were needed to further investigate the defect of cholic acid biosynthesis in patients with cerebrotendinous xanthomatosis (CTX).

journal_name

Steroids

journal_title

Steroids

authors

Dayal B,Bagan E,Speck J,Salen G

doi

10.1016/0039-128x(80)90144-0

subject

Has Abstract

pub_date

1980-04-01 00:00:00

pages

439-44

issue

4

eissn

0039-128X

issn

1878-5867

pii

0039-128X(80)90144-0

journal_volume

35

pub_type

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