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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (11): 1437-1441. 上一篇    下一篇

研究简报

保护的β-2-脱氧-2-氨基葡三糖的合成

郭振楚*,1，熊兴泉1,2   

  1. (1湖南科技大学化学化工学院 湘潭 411201)
    (2中国科学院化学研究所 北京 100080)
  • 收稿日期:2004-11-24 修回日期:2005-05-11 发布日期:2005-10-30
  • 通讯作者: 郭振楚

Synthesis of Protected 2-Amino-2-deoxytriglucose

GUO Zhen-Chu*,1,XIONG Xing-Quan1,2   

  1. (1 College of Chemistry and Chemical Engineering, Hunan University of Science and Tech-nology, Xiangtan 411201)
    (2 Institute of Chemistry, Chinese Academy of Sci-ences, Beijing 100080)
  • Received:2004-11-24 Revised:2005-05-11 Published:2005-10-30
  • Contact: GUO Zhen-Chu

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以茴香醛保护氨基方法得到的β-构型的四乙酰基氨基葡萄糖盐酸盐(1)为原料, 采用三氯乙酰基(TCA)、三氯乙酰亚胺酯基(TCI)和乙硫基(SEt)保护体系, 经五步反应以产率40.5%得到完全β-构型保护的β-(1→3)-2-脱氧-2-氨基葡二糖7, 又经两步合成得到保护的β-(1→3)-2-脱氧-2-氨基葡二糖受体8, 共八步合成了保护的β-(1→3)-2-脱氧-2-氨基葡三糖10, 总产率为27%. 以上化合物均为未知. 同时, 还得到了用以合成β-(1→4)-保护的氨基葡四糖的受体6. 采用该保护体系可以高选择性地、较高产率地合成氨基寡糖.

关键词: 氨基葡萄糖盐酸盐, 乙硫醇, 2-脱氧-2-氨基葡三糖, 三氯乙酰亚胺酯, 三氯乙酰氯

By using trichloroacetyl, trichloroacetimidate group and ethylthio as the protection system and through five steps, protected β-(1→3)-2-amino-2-deoxydiglucose 7 was synthesized from β-tetra-O-acetyl-glucosylamine hydrochloride (1). β-(1→3)-2-amino-2-deoxydiglucose acceptor 8 was also produced by two steps. Finally protected β-(1→3)-2-amino-2-deoxytriglucose 10 was obtained through eight steps with the tolal yield of 27%. These compounds are all new ones. Using this protection system, amino- oligosaccharides can be selectively synthesized with high yield.

Key words: glucosylamine hydrochloride, trichloroacetyl chloride, trichloroacetimidate, ethanethiol, 2-amino-2-deoxyl-triglucose