高等学校化学学报

高等学校化学学报 ›› 1999, Vol. 20 ›› Issue (10): 1554.

• 论文 • 上一篇    下一篇

N-苄基-3(S)-邻苯二甲酰亚胺基-4(S)-[4(S)-2,2-二甲基-1,3-二氧环戊-4-基]-2-氧吖丁啶的合成

李恒光1,2, 吴彤2, 谢如刚1, 胡键1, 王建伟1,2, 胡晓斌3   

  1. 1. 四川大学化学系, 成都 610064;
    2. 四川抗菌工业研究所, 成都 610051;
    3. 华西医科大学药学院, 成都 610041
  • 收稿日期:1998-10-12 出版日期:1999-10-24 发布日期:1999-10-24
  • 通讯作者: 谢如刚
  • 作者简介:李恒光,男,36岁,博士研究生.
  • 基金资助:

    国家自然科学基金(批准号:29632004);国家新药研究基金(批准号:969010581)资助课题

Synthesis of N-Benzyl-3(S)-phthalimido-4(S)-[4(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-azetidine

LI Heng-Guang1,2, WU Tong2, XIE Ru-Gang1, HU Jian1, WANG Jian-Wei1,2, HU Xiao-Bin3   

  1. 1. Department of Chemistry, Sichuan University, Chengdu 610064, China;
    2. Sichuan IndustriaLINstitute of Antibiotics, Chengdu 610051, China;
    3. Pharmacy School of West China University of Medicine Sciences, Chengdu 610041, China
  • Received:1998-10-12 Online:1999-10-24 Published:1999-10-24

PDF (PC)

被引次数

4

摘要： 以L-抗坏血酸(1)为原料,经3步反应制得(S)-缩异丙氧叉甘油醛(4).该手性醛与苄胺缩合制得相应的手性亚胺(5).甘氨酸经保护后制成酰氯,在有机碱作用下首先生成不稳定的烯酮(8),继与手性亚胺5迅速进行[2+2]环加成反应,合成标题化合物N-苄基-3(S)-邻苯二甲酰亚胺基-4(S)-[4(S)-2,2-二甲基-1,3-二氧环戊-4-基]-2-氧吖丁啶.由于环加成的面向立体选择性容易控制,由此所得产物的光学纯度和化学收率均较高

关键词: &beta, -内酰胺, L-抗坏血酸, 手性亚胺, 烯酮, [2+2]环加成反应

Abstract: (S)-Glyceraldehyde acetonide 4 which is a very useful chiraLINtermidiate in stere-oselective synthesis was prepared conveniently by a new three-step synthetic method from natural chiral resource of L-ascorbic acid 1. The chiral aldehyde condensed with benzyl amine to produce adapted chiraLImine 5. The imine is unstable, but it can carry a [2+2] cyclic addition with ketene 8 which was obtained from phthalimidoacetyl chloride and triethylamine under mild conditions, and produce the title compound, N-benzyl-3-(S)-phthalimido-4-(S)-[4(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-azetidine. Because of the high facial stereoselection in cyclic addition mechanism and attacking with ketene in unblocked face of the imine, the optical purity of the final product is quite satisfactory.

Key words: β-Lactam, L-Ascorbic acid, ChiraLImine, Ketene, [2+2] Cyclic addition

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