Synthesis of selenium-linked neoglycoconjugates and pseudodisaccharides

被引：23

作者：

Affeldt, Ricardo F. ^{[1
]}

Braga, Hugo C. ^{[2
]}

Baldassari, Lucas L. ^{[1
]}

Luedtke, Diogo S. ^{[1
,2
]}

机构：

[1] Univ Fed Rio Grande do Sul, Inst Quim, BR-91501970 Porto Alegre, RS, Brazil

[2] Univ Sao Paulo, Fac Ciencias Farmaceut, Sao Paulo, Brazil

来源：

TETRAHEDRON | 2012年 / 68卷 / 51期

基金：

巴西圣保罗研究基金会;

关键词：

Selenocarbohydrates; Neoglycoconjugates; Pseudodisaccharides; Chiral selenium compounds; STEREOSELECTIVE-SYNTHESIS; INHIBITORY-ACTIVITIES; EFFICIENT SYNTHESIS; AMINO DISELENIDES; NUCLEIC-ACIDS; SELENOGLYCOSIDES; ORGANOSELENIUM; NUCLEOSIDES; ANALOGS; OLIGONUCLEOTIDES;

D O I：

10.1016/j.tet.2012.08.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The introduction of organoselenium moieties within the structure of carbohydrates has received attention recently. Herein, we report on the synthesis of selenium-containing neoglycoconjugates and pseudodisaccharides by the reaction of nucleophilic selenium species, generated from sugar diselenides, with chiral N-Boc aziridines and sugar tosylates. The reaction proceeds with moderate to good yields for various substrates. The introduction of organoselenium moieties within the framework of various sugars, with increased levels of complexity, thus allowing the synthesis of disaccharide and glycoconjugate mimetics. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：10470 / 10475

页数：6

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