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

被引：7

作者：

DAYAL, B

SALEN, G

PADIA, J

SHEFER, S

TINT, GS

WILLIAMS, TH

TOOME, V

SASSO, G

机构：

[1] UNIV MED & DENT NEW JERSEY,NEW JERSEY MED SCH,DEPT MED,NEWARK,NJ 07103

[2] HOFFMANN LA ROCHE INC,ROCHE RES CTR,NUTLEY,NJ 07110

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 1992年 / 61卷 / 03期

关键词：

BILE ALCOHOLS; ASYMMETRIC SYNTHESIS; LANTHANIDE-INDUCED CD; COTTON EFFECT; H-1-NMR AND C-13-NMR;

D O I：

10.1016/0009-3084(92)90107-Z

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 H-1 and C-13-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.

引用

页码：271 / 281

页数：11

共 50 条

[1] STEREOSELECTIVE SYNTHESIS AND STRUCTURE PROOF OF (24R)-5-BETA-CHOLESTANE-3-ALPHA, 7-ALPHA, 12-ALPHA, 24,25 -PENTOL AND 25(S) -5-BETA-CHOLESTANE-3-ALPHA, 7-ALPHA, 12-ALPHA, 25,26-PENTOL
DAYAL, B
SALEN, G
PADIA, J
TOOME, V
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 198 : 74 - MEDI
[2] STEREOSELECTIVE SYNTHESIS OF THE 24R-DIASTEREOISOMERS AND 24S-DIASTEREOISOMERS OF 5-BETA-CHOLESTANE-3-ALPHA, 7-ALPHA, 12-ALPHA, 24, 25-PENTOLS
BATTA, AK
AGGARWAL, SK
SALEN, G
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 197 : 18 - MEDI
[3] ASYMMETRIC SYNTHESES AND LANTHANIDE-INDUCED CD STUDIES OF (24R AND 24S) 5-BETA-CHOLESTANE-3-ALPHA, 7-ALPHA, 12-ALPHA, 24, 25-PENTOLS
DAYAL, B
RAO, K
SALEN, G
SEONG, WM
PRAMANIK, BN
HUANG, EC
TOOME, V
PURE AND APPLIED CHEMISTRY, 1994, 66 (10-11) : 2037 - 2040
[4] SYNTHESIS OF THE PUTATIVE METABOLITES OF PLANT STEROLS - (24R) AND (24S)-24-METHYL-5-BETA-CHOLESTANE-3-ALPHA,7-ALPHA,12-ALPHA,25-TETROLS AND 24-ETHYL-5-BETA-CHOLESTANE-3-ALPHA,7-ALPHA,12-ALPHA,24-ZETA-TETROL
DAYAL, B
SALEN, G
TINT, GS
BATTA, AK
SHEFER, S
JOURNAL OF LIPID RESEARCH, 1984, 25 (08) : 865 - 870
[5] A FACILE SYNTHESIS OF 5-BETA-CHOLESTANE-3-ALPHA, 7-ALPHA, 12-ALPHA, 25-TETROL
DAYAL, B
BAGAN, E
SPECK, J
SALEN, G
STEROIDS, 1980, 35 (04) : 439 - 444
[6] PREPARATION OF 24(R) AND 24(S)-5-BETA-CHOLESTANE-3-ALPHA,7-ALPHA,24-TRIOLS AND 25(R) AND 25(S)-5-BETA-CHOLESTANE-3-ALPHA,7-ALPHA,26-TRIOLS BY A HYDROBORATION PROCEDURE
DAYAL, B
BATTA, AK
SHEFER, S
TINT, GS
SALEN, G
MOSBACH, EH
JOURNAL OF LIPID RESEARCH, 1978, 19 (02) : 191 - 196
[7] PREPARATION AND CHARACTERIZATION OF (24R AND 24S)-5-BETA-CHOLESTANE-3-ALPHA,7-ALPHA,24,25-TETROLS AND (24R AND 24S)-5-BETA-CHOLESTANE-3-ALPHA,24,25-TRIOLS
BATTA, AK
DAYAL, B
TINT, GS
SHEFER, S
TOOME, V
SALEN, G
MOSBACH, EH
STEROIDS, 1978, 31 (01) : 99 - 111
[8] BILE ALCOHOL GLUCURONIDES - REGIOSELECTIVE O-GLUCURONIDATION OF 5-BETA-CHOLESTANE-3-ALPHA, 7-ALPHA, 12-ALPHA, 25-TETROL AND 24-NOR-5-BETA-CHOLESTANE-3-ALPHA, 7-ALPHA, 12-ALPHA, 25-TETROL
DAYAL, B
SALEN, G
PADIA, J
SHEFER, S
TINT, GS
SASSO, G
WILLIAMS, TH
CARBOHYDRATE RESEARCH, 1993, 240 : 133 - 142
[9] IDENTIFICATION OF 5-BETA-CHOLESTANE-3-ALPHA,7-ALPHA,12-ALPHA,24,25,26-HEXOL IN HUMAN-URINE
HIRAOKA, T
KIHIRA, K
KAJIYAMA, G
KURAMOTO, T
HOSHITA, T
JOURNAL OF LIPID RESEARCH, 1987, 28 (08) : 895 - 899
[10] IDENTIFICATION OF 5-BETA-CHOLESTANE-3-ALPHA, 7-ALPHA, 12-ALPHA, 25, 26-PENTOL IN CEREBROTENDINOUS XANTHOMATOSIS
DAYAL, B
TINT, GS
GREELEY, DN
WILLIAMS, TH
SALEN, G
STEROIDS, 1983, 42 (04) : 441 - 448

← 1 2 3 4 5 →