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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (03): 467-471. 上一篇    下一篇

研究论文

糖基修饰的氨基酸类化合物的合成

钱兆生a，周传健b，李根a，曹玲华*,a   

  1. (a新疆大学化学化工学院 乌鲁木齐 830046)
    (b山东大学材料学院 济南 250061)
  • 收稿日期:2006-07-18 修回日期:2007-10-03 发布日期:2008-03-18
  • 通讯作者: 曹玲华

Synthesis of Glycose-Containing Amino Acid Derivatives

QIAN Zhao-Shenga,ZHOU Chuan-Jianb,LI Gena,CAO Ling-Hua*,a   

  1. (a College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046)
    (b School of Material Science and Technology, Shandong University, Jinan 250061)
  • Received:2006-07-18 Revised:2007-10-03 Published:2008-03-18
  • Contact: CAO Ling-Hua

PDF

881

被引次数

10

通过对5种氨基酸酯化和氨基保护得到苄氧羰基氨基酸甲酯, 经肼解制备苄氧羰基氨基酸酰肼, 然后分别与3种不同的糖基异硫氰酸酯反应, 制备了相应的目标化合物15个, 且产率均在60%以上. 所有新化合物均经元素分析, IR, MS和1H NMR确证. 同时探索了苄氧羰基氨基酸甲酯肼解的最佳反应条件.

关键词: 糖基异硫氰酸酯, L-α-氨基酸, 酰肼, 合成 Synthesis of Glycose-Containing

Fifteen target compounds were synthesized with the following three steps: amino acids were protected to form carbobenzoxyamino acid methyl esters, the carbobenzoxyamino acid methyl esters reacted with hydrazine to give carbobenzoxy amino acid hydrazides, and treatment of the carbobenzoxy amino acid hydrazides with glycosyl isothiocyanates afforded 3a～3o in 65%～86% yields. All the new compounds were characterized by elemental analysis, MS, IR and 1H NMR spectra. Besides, the optimal reaction condition of the hydrazinolysis of carbobenzoxyamino acid methyl esters was studied.

Key words: L-α-amino acid, hydrazide, glycosyl isothiocyanate, synthesis