Synthesis of (25R)-[26-2H1]cholesterol and 1H n.m.r. and h.p.l.c. resolution of (25R)- and (25S)-26-hydroxycholesterol
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 1713-1718
- https://doi.org/10.1039/p19870001713
Abstract
Yamogenin acetate (1) was isolated from crude diosgenin acetate and converted into (25S)-26-hydroxycholesterol (6a). The absolute configuration at C-25 of (6a) was determined by X-ray crystallography. (25R)-[26-2H1] Cholesterol (10) was prepared by reduction of the 26-tosyloxy group by LiAl2H4. Reverse-phase h.p.l.c. resolution without derivatiration was developed for the diastereoisomers, (25R)- and (25S)-26-hydroxycholesterol. The (+)- or (–)-MTPA esters of these diastereoisomers showed distinctive 1H n.m.r. signals for 26-H.This publication has 8 references indexed in Scilit:
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