SYNTHETIC ROUTE FOR C-14 LABELING OF A BIOACTIVE LIPID-A ANALOG

被引：14

作者：

FUKASE, K

AOKI, Y

KINOSHITA, I

SUDA, Y

KUROSAWA, M

ZAHRINGER, U

RIETSCHEL, ET

KUSUMOTO, S

机构：

[1] OSAKA UNIV,FAC SCI,DEPT CHEM,TOYONAKA,OSAKA 560,JAPAN

[2] FORSCHUNGSINST BORSTEL,D-23845 BORSTEL,GERMANY

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 47期

关键词：

D O I：

10.1016/0040-4039(95)01863-D

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic route for C-14-labeling of a phosphonooxyethyl (PE) analogue of E. coli lipid A was established by cold experiments. The PE analogue is chemically more stable than natural lipid A but shows practically identical biological activity. The glycosidation of ethylene glycol unit as the C-14-labeled position was effected with a disaccharide thioglycoside by use of a hypervalent iodine reagent, PhIO-SnClO4-AgClO4, as an activator. p-Methoxybenzyl group used for the protection of the distal hydroxyl group of ethylene glycol was selectively removed by trimethylsilyl triflate in CH3CN-CH2Cl2 followed by phosphorylation and deprotection gave the target compound.

引用

页码：8645 / 8648

页数：4

共 17 条

[1] IODOSOBENZENE-TRIFLIC ANHYDRIDE AS AN EFFICIENT PROMOTER FOR GLYCOSIDATION REACTION USING THIOGLYCOSIDES AS DONORS [J].