(1R,4R,5S)-5-exo-azido-2-chloro-7-oxabicyclo<2.2.1>hept-2-ene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (1R,4R,5S)-5-exo-azido-2-chloro-7-oxabicyclo<2.2.1>hept-2-ene
• 英文别名: (1R,4R,5S)-5-azido-2-chloro-7-oxabicyclo[2.2.1]hept-2-ene
• 化学式: C₆H₆ClN₃O
• 分子量: 171.586
• InChiKey: BPYJJNKPWNYZBC-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 (1R,4R,5S)-5-exo-azido-2-chloro-7-oxabicyclo<2.2.1>hept-2-ene 、 原甲酸三甲酯 生成 methyl 2,5-anhydro-3-azido-3,4-dideoxy-L-ribo-hexouronate dimethyl acetal
  参考文献：
  名称：

  Total, asymmetric synthesis of (1r-1-c-(6′-amino-7′h-purin-8′-yl)-1,4-anhydro-3-azido-2,3-dideoxy-d-erythro-pentitol.

  摘要：

  The "naked sugar" (+)-(1R,2R,4R)-2-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-exo-yl acetate ((+)-3) was converted in ten synthetic steps into the new C-nucleoside (1R)-1-C-(6'-amino-7'H-purin-8'-yl)-1,4-anhydro-3-azido-2,3-dideoxy-D-erythro-pentitol ((+)-2) in 19% overall yield.

  DOI：

  10.1016/s0040-4020(01)88359-9
• 作为产物：
  描述：

  (1R,2R,4R)-5-chloro-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl trifluoromethanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以95.5%的产率得到(1R,4R,5S)-5-exo-azido-2-chloro-7-oxabicyclo<2.2.1>hept-2-ene
  参考文献：
  名称：

  Total, asymmetric synthesis of (1r-1-c-(6′-amino-7′h-purin-8′-yl)-1,4-anhydro-3-azido-2,3-dideoxy-d-erythro-pentitol.

  摘要：

  The "naked sugar" (+)-(1R,2R,4R)-2-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-exo-yl acetate ((+)-3) was converted in ten synthetic steps into the new C-nucleoside (1R)-1-C-(6'-amino-7'H-purin-8'-yl)-1,4-anhydro-3-azido-2,3-dideoxy-D-erythro-pentitol ((+)-2) in 19% overall yield.

  DOI：

  10.1016/s0040-4020(01)88359-9

文献信息

• Total, asymmetric synthesis of (1r-1-c-(6′-amino-7′h-purin-8′-yl)-1,4-anhydro-3-azido-2,3-dideoxy-d-erythro-pentitol.
  作者：Vincent Jeanneret、Fabrizio Gasparini、Péter Péchy、Vogel Pierre

  DOI：10.1016/s0040-4020(01)88359-9

  日期：1992.11

  The "naked sugar" (+)-(1R,2R,4R)-2-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-exo-yl acetate ((+)-3) was converted in ten synthetic steps into the new C-nucleoside (1R)-1-C-(6'-amino-7'H-purin-8'-yl)-1,4-anhydro-3-azido-2,3-dideoxy-D-erythro-pentitol ((+)-2) in 19% overall yield.