Synthesis of novel 3-[(1-glycosyl-1H-1,2,3-triazol-4-yl)- methylamino]ket-2-en-1-ones

被引：2

作者：

Kumar, Banty ^{[1
,2
]}

Maity, Jyotirmoy ^{[1
]}

Kumar, Amit ^{[1
]}

Khatri, Vinod ^{[1
]}

Shankar, Bhawani ^{[1
]}

Prasad, Ashok K. ^{[1
]}

机构：

[1] Univ Delhi, Dept Chem, Bioorgan Lab, Delhi 110007, India

[2] Univ Delhi, Dept Chem, Rajdhani Coll, Delhi 110007, India

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2018年 / 54卷 / 03期

关键词：

N-glycoconjugates; CuAAC reaction; Sonogashira reaction; CLICK CHEMISTRY; INHIBITORS; DERIVATIVES; TRIAZOLES; ANALOGS; AZIDES;

D O I：

10.1007/s10593-018-2274-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nine 3-[(1-beta-D-ribofuranosyl- and 3-[(1-beta-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)methylamino]ket-2-en-1-ones have been synthesized by copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction between propargylamine derivatives and 1-azido-2,3,5-tri-O-benzoyl beta-D-ribofuranose or 2,3,4,6-tetra-O-acetyl-1-azido-beta-D-glucopyranose, followed by deprotection of the resulting tri-O-benzoyl- or tetraO-acetyl-1-beta-D-glycosyltriazoles in good yields. The precursor propargylamine derivatives were synthesized by Sonogashira reaction of substituted acetylenes and benzoyl chloride followed by Michael-type addition of propargylamine to the resulting substituted alkynes in good yields. The precursor azido sugars, 1-azido-2,3,5-tri-O-benzoyl-beta-D-ribofuranose and 2,3,4,6-tetra-O-acetyl-1-azido-beta-D-glucopyranose, were synthesized by azidation of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose and beta-D-glucopyranose pentacetate, respectively, with azidotrimethylsilane in the presence of tin(IV) chloride. All products were unambiguously characterized on the basis of the spectral data analysis.

引用

页码：362 / 368

页数：7

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