DESIGN AND SYNTHESIS OF A TRISUBSTRATE ANALOG FOR ALPHA(1-]3)FUCOSYLTRANSFERASE - A POTENTIAL INHIBITOR

被引：35

作者：

HESKAMP, BM

VEENEMAN, GH

VANDERMAREL, GA

VANBOECKEL, CAA

VANBOOM, JH

机构：

[1] LEIDEN UNIV,GORLAEUS LABS,LEIDEN INST CHEM,2300 RA LEIDEN,NETHERLANDS

[2] NV ORGANON,SCI DEV GRP,5430 BH OSS,NETHERLANDS

来源：

TETRAHEDRON | 1995年 / 51卷 / 30期

关键词：

D O I：

10.1016/0040-4020(95)00451-D

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phenyl 1-azido-3, 4,5-tri-O-benzyl-1-deoxy-2-seleno-alpha-L-fuco-heptulopyranoside (5), readily accessible from perbenzylated L-fucono-1,5-lactone, is a key intermediate in the preparation of trisubstrate analogue 2. NIS mediated condensation of fucosyl donor 5 with methyl 2,4,6-tri-O-benzyl-alpha-D-glucopyranoside (7) and ensuing reduction of the azido function furnished ketodisaccharide 10b, which was elongated at the 1-amino group of the fucose residue with a malonic acid spacer. The thus obtained compound was deprotected and subsequently coupled with 5'-amino-5'-deoxy-guanosine to afford the target compound 2.

引用

页码：8397 / 8406

页数：10

共 24 条

[1] SYNTHESIS OF CARBOCYCLIC ANALOGS OF GUANOSINE 5'-(BETA-L-FUCOPYRANOSYL DIPHOSPHATE) (GDP-FUCOSE) AS POTENTIAL INHIBITORS OF FUCOSYLTRANSFERASES [J].