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Synthesis of 21-(3-Methylbutyl)cholest-5-ene-3β,3′,25-triol and 21-(2-Methylpropoxy)cholest-5-ene-2′,3β,25-triol, the First “Double Side Chain” Cholesterol Analogues

✍ Scribed by Kurek-Tyrlik, Alicja ;Makaeva, Fliur Z. ;Wicha, Jerzy ;Calverley, Martin J.

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
518 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The 21‐(3‐hydroxy‐3‐methylbutyl)‐ and 21‐(2‐hydroxy‐2‐methylpropoxy)cholestane derivatives 3 and 5, formally double chain hybrid (20__R__)‐ and (20__S__)‐cholesterol analogues, were synthesized. The C‐22 to C‐27 section of the 25‐hydroxycholestane side chain was established by stereoselective alkylation with 5‐bromo‐2‐methyl‐2‐(triethylsilyl)oxypentane of the pregnanoic ester 8, derived from 3β‐acetoxyandrost‐5‐en‐17‐one (7). Reduction of the ester 9 to the 21‐alcohol 10 permitted elaboration of a second hydroxylated side chain, either via the tosylate 11 by alkynation/hydrogenation (yielding intermediate 13) or by alkylation of 10 with bromoacetate (yielding 14) followed by reaction with methyl magnesium bromide.

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