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Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (3): 325-327. Previous Articles     Next Articles

一种新的选择性氧化苏-(1S,2S)-2-(N,N-二甲胺基)-1-(对硝基苯基)-1,3-丙二醇的N-甲基为N-甲酰基的方法

单自兴*, 卢国坚   

  1. 武汉大学化学与分子科学学院 武汉 430072
  • 收稿日期:2003-06-02 修回日期:2003-08-22 接受日期:2003-09-26 发布日期:2022-09-20
  • 基金资助:
    国家自然科学基金(No. 29972033)资助项目

A New Selective Oxidation of N-Methyl to N-Formyl upon threo-(1S,2S)- 2-(N,N-Dimethylamino)-1-(4′-nitrophenyl)-1,3-propanediol

SHAN, Zi-Xing*, LU, Guo-Jian   

  1. Department of Chemistry, Wuhan University, Wuhan 430072
  • Received:2003-06-02 Revised:2003-08-22 Accepted:2003-09-26 Published:2022-09-20
  • Contact: *E-mail: kenshan@public.wh.hb.cn; Fax: 027-87647617.

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A new chemoselective oxidation of N-methyl toN-formyl upon threo-(1S,2S)-2-(N,N-dimethylamino)-1-(4′-nitrophenyl)-1,3-propanediol was reported. In the presence of Na2HPO4, threo-(1S,2S)-2-(N,N-dimethylamino)-1-(4′-nitrophenyl)-1,3-propanediol (DMANP) was oxidized by a 717 anion exchange resin-supported bromine in a H2O-CCl4 system at 60 ℃ for 24 h to give threo-(1S,2S)-2-(N-formyl-N-methylamino)-1-(4′-nitrophenyl)-1,3-propanediol (FMANP) in 51% yield. This selective oxidation of N-methyl to N-formyl was observed for the first time in 2-amino-1,3-propanediol derivative chemistry.

Key words: threo-(1S,2S)-2-(N,N-dimethylamino)-1-(4′-nitrophenyl)-1,3-propanediol, oxidation, formylation, solid-supported bromine