Synthesis of sulfated trisaccharide ligands for the selectins

被引：38

作者：

Sanders, WJ ^{[1
]}

Manning, DD ^{[1
]}

Koeller, KM ^{[1
]}

Kiessling, LL ^{[1
]}

机构：

[1] UNIV WISCONSIN, DEPT CHEM, MADISON, WI 53706 USA

来源：

TETRAHEDRON | 1997年 / 53卷 / 48期

关键词：

D O I：

10.1016/S0040-4020(97)01024-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In a directed effort to elucidate the molecular factors responsible for selectin-mediated cell adhesion events as a basis for the generation of potent and specific inhibitors of these processes, we have synthesized a variety of sulfated analogs of the trisaccharide recognition epitopes Lewis a [Le(a): Gal beta 1-->3(Fuc alpha 1-->4)GlcNAc] and Lewis x [Le(x): Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc]. Our divergent synthetic route allows for the synthesis of gram quantities of these sulfated trisaccharides from common intermediates in 10-20% overall yields and in no more than 15 linear steps. In addition, we have anchored the reducing end of the Le(a) and Le(x) trisaccharide precursors with a beta-allyl aglycone, providing a single anomer of each final product and allowing for further modification into multivalent derivatives. (C) 1997 Elsevier Science Ltd.

引用

页码：16391 / 16422

页数：32

共 78 条

[31] ON THE DIRECT EPOXIDATION OF GLYCALS - APPLICATION OF A REITERATIVE STRATEGY FOR THE SYNTHESIS OF BETA-LINKED OLIGOSACCHARIDES [J].