Synthetic study of a bioactive H-3-labeled analogue of lipid A

被引：0

作者：

Fukase, K ^{[1
]}

Kinoshita, I ^{[1
]}

Suda, Y ^{[1
]}

Aoki, Y ^{[1
]}

Liu, WC ^{[1
]}

Oikawa, M ^{[1
]}

Kurosawa, M ^{[1
]}

Zahringer, U ^{[1
]}

Seydel, U ^{[1
]}

Rietschel, ET ^{[1
]}

Kusumoto, S ^{[1
]}

机构：

[1] FORSCHUNGSZENTRUM BORSTEL,D-23845 BORSTEL,GERMANY

来源：

SYNLETT | 1996年 / 03期

关键词：

lipid A; tritium labeling; phosphonooxyethyl analogue; endotoxin; thioglycoside;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A radio-labeled bioactive lipid A derivative was synthesized for the first time by H-3-labeling of a phosphonooxyethyl (PE) analogue. H-3-Labeling was effected via oxidation of the distal hydroxyl group of the ethylene glycol unit of a disaccharide intermediate and subsequent reduction of the resulting aldehyde by (NaBH4)-H-3. Phosphorylation of the labeled alcohol and deprotection gave the target compound. The glycosidation of an ethylene glycol unit with a thioglycoside was promoted by PhIO-SnCl4-AgClO4 to give the alpha-glycoside selectively.

引用

页码：252 / &

页数：4

共 15 条

[1] A STEREOSELECTIVE GLYCOSIDATION USING THIOGLYCOSIDES, ACTIVATION BY COMBINATION OF N-BROMOSUCCINIMIDE AND STRONG ACID SALTS [J].