A concise synthesis of sugar isoxazole conjugates

被引：21

作者：

Luginina, Jevgenija ^{[1
]}

Rjabovs, Vitalijs ^{[1
]}

Belyakov, Sergey ^{[2
]}

Turks, Maris ^{[1
]}

机构：

[1] Riga Tech Univ, Fac Mat Sci & Appl Chem, LV-1007 Riga, Latvia

[2] Latvian Inst Organ Synth, LV-1006 Riga, Latvia

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 39期

关键词：

Carbohydrates; Isoxazoles; Azoles; Glycoconjugates; Nitrile oxide; Dipolar cycloaddition; NITRILE OXIDE CYCLOADDITION; C-GLYCOSYL; 1,3-DIPOLAR CYCLOADDITIONS; BIOLOGICAL-ACTIVITIES; DERIVATIVES; INTERMEDIATE; NUCLEOSIDES; AGENTS; DEHYDRATION; INHIBITORS;

D O I：

10.1016/j.tetlet.2013.07.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of novel 3,5-disubstituted isoxazole-carbohydrate conjugates is described. The title compounds are obtained from 3-deoxy-3-C-nitromethyl derivatives of 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose via nitrile oxide intermediates. The developed approach provides the first examples of isoxazolyl sugars where the azole fragment is attached to C(3) of the carbohydrate through a C-C bond. Isoxazoles can be valuable linkers in glycoconjugate chemistry and this is demonstrated by the synthesis of a glycocluster containing five carbohydrate residues attached to a central glucose platform. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5328 / 5331

页数：4

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