Synthesis of 1,2,3-triazole-linked glycohybrids in the gluco-, gulo-, and allopyranose series

被引：5

作者：

Uzulena, Jevgenija ^{[1
]}

Rjabovs, Vitalijs ^{[1
]}

Moreno-Vargas, Antonio J. ^{[2
]}

Turks, Maris ^{[1
]}

机构：

[1] Riga Tech Univ, Inst Technol Organ Chem, LV-1048 Riga, Latvia

[2] Univ Seville, Fac Chem, Dept Organ Chem, E-41002 Seville, Spain

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2015年 / 51卷 / 07期

关键词：

allose; glucose; gulose; 1,2,3-triazole; click chemistry; extended bistriazolyl linker; furanose-pyranose equilibrium; galactosidase activators; BIOLOGICAL-ACTIVITY; TERMINAL ALKYNES; CLICK REACTION; DERIVATIVES; INHIBITORS; CHEMISTRY; TRIAZOLE; AZIDES; TRANSFORMATIONS; ACTIVATORS;

D O I：

10.1007/s10593-015-1754-x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ketone derived from diacetone-alpha-D-glucose is a suitable starting material for the synthesis of 3-C-linked glycohybrids containing 1,2,3-triazole moiety as an intersugar linkage. The pyranose tautomers of 3-deoxy-3-(1,2,3-1H-triazol-1-yl) glucose, 3-C-[(1,2,3-1H-triazol-1-yl) methyl] allose and 3-C-[(1,2,3-1H-triazol-1-yl) methyl] gulose moieties are released upon the acidic hydrolysis of the corresponding O-isopropylidene-protected furanosyl-type synthetic intermediates. Some of the title compounds show a rare property of activating beta-galactosidase from Escherichia coli.

引用

页码：664 / 671

页数：8

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