Stereoselective synthesis of (24R and 24S) 5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,25-pentols and (25R and 25S) 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25,26-pentols using a modified osmium-catalyzed Sharpless asymmetric dihydroxylation process.
Described herein are the stereoselective syntheses of the (24R, 24S) and (25R, 25S) isomers of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,25-pentols and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25,26-pentols by using a modified osmium-catalyzed Sharpless asymmetric dihydroxylation process. Also presented herein are the results of lanthanide-induced CD Cotton effect measurements and 1H- and 13C-nuclear magnetic resonance studies of (24R, 24S) and (25R, 25S)-5 beta-cholestanepentols and their derivatives. These compounds were required to study the biosynthesis of cholic acid from cholesterol.
Dayal
B
B
Dept. of Medicine, UMDNJ-New Jersey Medical School, Newark 07103.
Salen
G
G
Padia
J
J
Shefer
S
S
Tint
G S
GS
Williams
T H
TH
Toome
V
V
Sasso
G
G
D002777:Cholestanols / Q000138:chemical synthesis*; D006900:Hydroxylation; D009992:Osmium / Q000737:chemistry*; D013237:Stereoisomerism
D002777:Cholestanols; D009992:Osmium; C012832:cholestane-3,7,12,24,25-pentol; C006836:5 beta-bufol