Convenient synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter-solvent: Readily access to non-ionic triazolylglycoside surfactants for evaluation of cytotoxic activity

被引：6

作者：

Ketsomboon, Nutthanicha ^{[1
,2
]}

Saeeng, Rungnapha ^{[1
,2
,3
]}

Srisook, Klaokwan ^{[2
,4
,5
]}

Sirion, Uthaiwan ^{[1
,2
,3
]}

机构：

[1] Burapha Univ, Fac Sci, Dept Chem, Chon Buri 20131, Thailand

[2] Burapha Univ, Fac Sci, Ctr Excellence Innovat Chem, Chon Buri 20131, Thailand

[3] Burapha Univ, Res Unit Synthet Cpds & Synthet Analogues Nat Pro, Chon Buri 20131, Thailand

[4] Burapha Univ, Fac Sci, Dept Biochem, Chon Buri, Thailand

[5] Burapha Univ, Fac Sci, Res Unit Nat Bioact Cpds Healthcare Prod Dev, Chon Buri, Thailand

来源：

TETRAHEDRON LETTERS | 2021年 / 80卷

关键词：

Triazolylglycosides; Carbohydrate-based surfactants; Ionic liquids; Triazole ring; Click reaction; ONE-POT SYNTHESIS; SUGAR-BASED SURFACTANTS; CLICK-CHEMISTRY; ANTIMICROBIAL ACTIVITY; HUISGEN CYCLOADDITION; EFFICIENT SYNTHESIS; GLYCOSYL TRIAZOLES; FACILE SYNTHESIS; INHIBITORS; AZIDES;

D O I：

10.1016/j.tetlet.2021.153325

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient method for the one-pot synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter and solvent is described via a sequential one-pot two-step glycosidation-CuAAc click reaction. The reaction was carried out using commercially available substrates, including glycosyl bromides, sodium azide and various long alkyl-chain alkynes to achieve the corresponding products in moderate to high yields. Furthermore, this approach was successfully applied for the preparation of non-ionic monocatenary triazolylglycoside surfactants in excellent yields through simple deacetylation. Subsequently, these surfactants were further evaluated for their cytotoxic activity. (c) 2021 Elsevier Ltd. All rights reserved.

引用

页数：16