Preparation of CI-1027 glucuronide: Metabolite of a remarkable lipid-modulating agent

被引:10
作者
Akin, A [1 ]
Curran, TT [1 ]
机构
[1] Pfizer Global Res & Dev, Pharmaceut Sci, Ann Arbor, MI 48105 USA
关键词
O-acylglucuronide; enzymatic hydrolysis;
D O I
10.1081/SCC-200061648
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of the 1 beta-glucuronide of the diacid, CI-1027, is described. The key synthetic steps are coupling of the mono-protected acid with bromoglucuronide, deacetylation, and enzymatic hydrolysis.
引用
收藏
页码:1649 / 1661
页数:13
相关论文
共 13 条
[1]  
BIESALSKI HK, 1995, LIEBIGS ANN, P717
[2]   PREPARATION OF ARYLDIAZOALKANES BY BAMFORD-STEVENS REACTION [J].
FARNUM, DG .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (03) :870-&
[3]  
FIANDOR J, 1985, SYNTHESIS-STUTTGART, P1121
[4]   TRI-O-ACETYL-BETA-D-GLUCOPYRANURONO-6,1-LACTONE [J].
FRY, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (14) :3915-3916
[5]  
Gross S, 2000, J PRAKT CHEM, V342, P711, DOI 10.1002/1521-3897(200009)342:7<711::AID-PRAC711>3.3.CO
[6]  
2-D
[7]   A convenient synthesis of beta-acyl glucuronides [J].
Juteau, H ;
Gareau, Y ;
Labelle, M .
TETRAHEDRON LETTERS, 1997, 38 (09) :1481-1484
[8]   Semisynthesis of abrusoside A methyl ester [J].
Kim, NC ;
Kinghorn, AD ;
Kim, DSHL .
ORGANIC LETTERS, 1999, 1 (02) :223-224
[9]   Synthesis of C-terminal glycopeptides from resin-bound glycosyl azides via a modified Staudinger reaction [J].
Malkinson, JP ;
Falconer, RA ;
Toth, I .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5249-5252
[10]  
MCCLOSKEY CM, 1955, ORG SYNTH, V3, P435