Synthesis of β-D-Galf(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf(1-6)-D-GlcNAc by SnCl4-promoted glycosylation

被引：38

作者：

Gallo-Rodriguez, C ^{[1
]}

Gandolfi, L ^{[1
]}

de Lederkremer, RM ^{[1
]}

机构：

[1] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, CIHIDECAR, RA-1428 Buenos Aires, DF, Argentina

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 02期

关键词：

D O I：

10.1021/ol9905811

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. beta-D-Galf-(1-3)-D-GlcNAc (1) was prepared by employing the trichloroacetamidate procedure for the glycosylation step, The mild conditions of this reaction are appropriate for condensation of 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranosyl trichloroacetamidate (6) with acid-labile benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside (3). On the other hand, tin(IV) chloride promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (11) with penta-O-benzoyl-alpha,beta-D-galactofuranose (4) gave the derivative of beta-D-Galf-(1-6)-D-GlcNAc (2) in 78% yield.

引用

页码：245 / 247

页数：3

共 11 条

[1]

ALLEN PZ, 1962, METHODS CARBOHYDR CH, V1, P372

[2] Synthesis of some galactofuranosyl disaccharides using a galactofuranosyl trichloroacetimidate as donor [J].