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
收藏
页码：362 / 368
页数：7
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