A concise synthesis of N-trichloroethoxycarbonyl lactosamine trichloroacetimidate donor and its application in the synthesis of Gal(β1-4)GIcNAc(β1-3)L-Fuc(α-OAll)

被引：30

作者：

Xue, J ^{[1
]}

Khaja, SD ^{[1
]}

Locke, RD ^{[1
]}

Matta, KL ^{[1
]}

机构：

[1] New York State Dept Hlth, Roswell Pk Canc Inst, Buffalo, NY 14263 USA

来源：

SYNLETT | 2004年 / 05期

关键词：

glucosamine acceptor; lactosamine donor; N-trichloroethoxy; carbonyl (N-Troc); 2-naphthylmethyl (NAP); intermolecular aglycon transfer;

D O I：

10.1055/s-2004-820032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A large-scale practical approach is described for converting D-glucosamine into lactosamine donor. 2-Naphthylmethyl (NAP) functionality is utilized as anomeric protecting group of N-trichloroethoxycarboonyl (N-Troc) glucosamine, which can avoid an unexpected intermolecular aglycon transfer observed in TMSOTf-mediated glycosylation when using corresponding thioglycoside as glycosyl acceptor. N-Troc protected glucosamine 9 shows enhanced reactivity as glycosyl acceptor, which was confirmed by systemic comparison with various N-protected glucosamine derivatives in TMSOTf-mediated glycosylation. The lactosamine imidate 14 exhibits valuable glycosyl donor property for P-selective glycosylation which furnished the desired trisaccharide Gal(beta1-4)GlcNAc(beta1-3)L-Fuc(alpha-OAll) in high yield. This sequence is part of O-linked chains of human clotting factor IX and mammalian Notch 1, and it was also found to be required for fringe to inhibit Jagged I -dependent Notch activation.

引用

页码：861 / 865

页数：5

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