Journal of Lipid Research, Vol 25, 871-875, Copyright © 1984 by Lipid Research, Inc.
Absolute configuration at carbon 23 of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,23,25-pentol excreted by patients with cerebrotendinous xanthomatosis
K Kihira, A Kubota and T Hoshita
Absolute configuration at C-23 of 5 beta-cholestane-3 alpha,7 alpha,12
alpha,23,25-pentol, one of the bile alcohols isolated from the patients
with cerebrotendinous xanthomatosis, was unequivocally determined as 23S by
conversion of a key intermediate, (23S)-5 beta-cholest-25-ene-3 alpha,7
alpha,12 alpha,23-tetrol to either the bile alcohol of known absolute
configuration, (23R)-5 beta-cholestane-3 alpha,7 alpha,12 alpha,23-tetrol,
or the naturally occurring 23,25-pentol.