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有机化学 ›› 2007, Vol. 27 ›› Issue (06): 744-748. 上一篇    下一篇

研究论文

N-糖基-N'-酰氨基硫脲及其环合产物的合成

田添a，曹玲华*,a,b，钱兆生a   

  1. (a新疆大学化学化工学院 乌鲁木齐 830046)
    (b南开大学元素有机化学国家重点实验室 天津 300071)
  • 收稿日期:2006-08-22 修回日期:2006-10-17 发布日期:2007-05-21
  • 通讯作者: 曹玲华

Synthesis of N-Glycosyl-N'-amido Thioureas and Their RelatedHeterocyclic Compounds

TIAN Tiana, CAO Ling-Hua*,a,b, QIAN Zhao-Shenga   

  1. (a College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046)
    (b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071)
  • Received:2006-08-22 Revised:2006-10-17 Published:2007-05-21
  • Contact: CAO Ling-Hua

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1021

以L-α-氨基酸为起始原料, 经酯化、氨基保护、肼解制得N-对甲苯磺酰基-L-α-氨基酸酰肼2, 再与糖基异硫氰酸酯3～5反应, 得到9种新型N-糖基-N'-酰氨基硫脲6～8, 然后在Hg(OAc)2/EtOH条件下关环, 合成了一系列新的2-对甲苯磺酰氨基烃基-5-糖氨基-1,3,4-噁二唑类化合物9～11. 所有新化合物的结构均经IR, 1H NMR, MS谱和元素分析确证.

关键词: 氨基酸酰肼, 1,3,4-噁二唑, 糖基异硫氰酸酯, 酰氨基硫脲, L-α-氨基酸

The starting material L-α-amino acids were converted into N-p-toluenesulfonyl-L-α-amino acid hydrazides 2 through following steps, esterification, amino protection and hydrazinolysis. The reaction of 2 with glycosyl isothio-cyanates 3～5 gave the novel compounds, N-glycosyl-N'-amido thioureas 6～8. The compounds 6～8 were cyclized under the system of Hg(OAc)2/EtOH to afford a series of new compounds, 2- p-toluenesulfonylaminoalkyl-5-glycosylamino-1,3,4-oxadiazoles 9～11. The structures of the new compounds were confirmed by IR, 1H NMR, MS spectra and elemental analysis.

Key words: amino acid hydrazide, 1,3,4-oxadiazole, glycosyl isothiocyanate, amido thiourea, L-α-amino acid