Premium
New bile alcohols II: Synthesis and mass spectra of C 26 bile alcohols
Author(s) -
Kuramoto Taiju,
Cohen Bertram I.,
Mosbach Erwin H.
Publication year - 1977
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf03027639
Subject(s) - cholestane , chemistry , acetic anhydride , hydrolysis , acetic acid , chromatography , organic chemistry , column chromatography , catalysis
and Summary The synthesis of (23α‐) and (23β‐)24‐nor‐5β‐cholestane‐3α,7α,23,25‐tetrols (VII‐a and VII‐b) and 24‐nor‐5β‐cholestane‐3α,7α,25,26‐tetrol (VIII) is described. Dehydration of 24‐nor‐5β‐cholestane‐3α,7α,25‐triol (II) (synthesized from methyl chenodeoxycholate via a Grignard reaction) with acetic anhydride and acetic acid yielded two unsaturated compounds. These were oxidized with osmium tetroxide to produce a mixture of 24‐nor‐5β‐cholestane‐3α,7α‐diacetoxy‐23ξ,25‐diol (V) and 24‐nor‐5β‐cholestane‐3α,7α‐diacetoxy‐25,26‐diol (VI). After separating these diols (V and VI) by column chromatography, each compound was hydrolyzed with KOH to give 24‐nor‐5β‐cholestane‐3α,7α,23ξ,25‐tetrol (VII) and 24‐nor‐5β‐cholestane‐3α,7α,25,26‐tetrol (VIII), respectively. Two isomers of the tetrol (VII) were separated using alumina column chromatography (VII‐a and VII‐b).