Synthesis of monomeric methylene-linked 1,2,3-triazole glycoconjugates from allo- and glucofuranoses

被引：6

作者：

Grigorjeva, Jelena ^{[1
]}

Uzulena, Jevgenija ^{[1
]}

Rjabovs, Vitalijs ^{[1
]}

Turks, Maris ^{[1
]}

机构：

[1] Riga Tech Univ, Fac Mat Sci & Appl Chem, Inst Technol Organ Chem, 3-7 P Valdena St, LV-1048 Riga, Latvia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2015年 / 51卷 / 10期

关键词：

diacetone glucose; diacetone allose; carbohydrate triazole conjugates; click chemistry; CuAAC; BIOLOGICAL-ACTIVITY; ALPHA-GLUCOSIDASES; TERMINAL ALKYNES; DERIVATIVES; INHIBITORS; AGENTS; AZIDES; NUCLEOSIDE;

D O I：

10.1007/s10593-015-1791-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbohydrate-triazole conjugates proved themselves as valuable enzyme activity-modifying agents. Recent exploration of nontrivial conjugates in which the bonding is formed not at the glycosidic or terminal carbons of the carbohydrates, but at C-3 position showed a potential of this type of structures as the ligands for various glycosidases and galectins. Here, we report synthesis of protected monomeric 3-C-(triazolylmethyl)-substituted gluco- and alloconjugates. Diastereomeric azides are synthesized from common intermediate, 3-deoxy-1,2:5,6-di-O-isopropylidene-3-oxo-alpha-D-allofuranose, and used in Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reactions with commercial alkynes. The yields of the cycloaddition reactions are good to excellent under different catalytic conditions.

引用

页码：883 / 890

页数：8

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