Synthesis of novel multidentate carbohydrate-triazole ligands

被引：50

作者：

Ziegler, Thomas ^{[1
]}

Hermann, Catrin ^{[1
]}

机构：

[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 13期

关键词：

D O I：

10.1016/j.tetlet.2008.01.081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cu(I)-catalyzed 1,3-dipolar cycloaddition (click reaction) of 1 mol equiv of N,N'-di-prop-2-ynyl-phthalamide (1a), N,N'-di-prop-2-ynyl-isophthalamide (1b), and pyridine-2,6-dicarboxylic acid bis-prop-2-ynylamide (1c), respectively with 2 mol equiv of 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide (2a), 2-azidoethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (2b), and 2-azidoethyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (2c), respectively, afforded the corresponding bis-cycloadducts 3-5, containing two 1,2,3-triazole moieties each, in 38-76% yield. Reaction of 1 mol equiv of 2c with 1 mol equiv of le under otherwise identical conditions gave the mono-cycloadduct 6, containing one 1,2,3-triazole and one 2-propynylamide moiety, in 77% yield. Reaction of 6 with 2a afforded 7, containing two different sugar moieties, in 67% yield. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2166 / 2169

页数：4

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