Synthesis of 'reversed' pyrimidine and pyrazolo [1,5-a]pyrimidine-C-nucleoside analogues from push-pull functionalized α-D-xylo-hept-5-ulofuranurononitrile

被引:1
|
作者
Hashmi, Imran Ali [1 ]
Ali, Firdous Lmran
Feist, Holger
Michalik, Manfred
Reinke, Helmut
Peseke, Klaus
机构
[1] Univ Karachi, Dept Chem, Karachi 75270, Pakistan
[2] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[3] Leibniz Inst Organ Katalyse, D-18059 Rostock, Germany
来源
SYNTHESIS-STUTTGART | 2007年 / 18卷 / 18期
关键词
enzyme inhibitors; C-nucleosides; monosaccharide derivatives; cyclization; pyrazoles;
D O I
10.1055/s-2007-983879
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-6-[bis(methylsulfanyl)methylene]-alpha-D-xylo-hept-5-ulofuranurononitrile (1) was reacted with acetamidinium chloride, S-methylisothiouronium sulfate, and guanidinium chloride, respectively, in the presence of triethylamine to furnish the 2-substituted 4-(3-O-benzyl-1,2-O-isopropylidene-alpha-D-xylo-tetrofuranos-4-yl)-6-methylsulfanylpyrimidine-5-carbonitriles 2a-c. Treatment of I with different 5-aminopyrazole-4-carboxylic acid derivatives yielded the 8-(3-O-benzyl-1,2-O-isopropylidene-alpha-D-xylo-tetrofuranos-4-yl)-6-methylsulfanylpyrazolo[1,5-a]pyrimidine-3,7-dicarboxylic acid derivatives 3a-c.
引用
收藏
页码:2819 / 2822
页数:4
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