(1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carbonyl azide | 158262-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carbonyl azide
• CAS: 158262-95-4
• 化学式: C₉H₁₃N₃O₃
• 分子量: 211.221
• InChiKey: BBWHQQOJLIDDPY-DSYKOEDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carbonyl azide 在 吡啶 、 氨 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 (E)-N-[[(1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropyl]carbamoyl]-3-methoxyprop-2-enamide
  参考文献：
  名称：

  Asymmetric Synthesis of (1'S,2'R)-Cyclopropyl Carbocyclic Nucleosides

  摘要：

  Enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been accomplished. The key intermediates 7 and 9 were synthesized from D-glyceraldehyde acetonide 1, which was converted to the alpha,beta-unsaturated ester 2 and then reduced to give allylic alcohol 3a. Stereoselective construction of the cyclopropyl ring of 3a and 3b followed by oxidation gave acid 5, which was treated under Curtius rearrangement conditions to obtain the urea intermediate 7. The urea intermediate was utilized to prepare uracil 14, thymine 15, and cytosine 18 nucleosides. The purine derivatives were prepared from cyclopropylamine 9 by condensation with 4,6-dichloro-5-form-amidopyrimidine or 4,6-dichloro-2-aminopyrimidine.

  DOI：

  10.1021/jo00121a047
• 作为产物：
  描述：

  (1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carboxylic acid 在 sodium azide 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 (1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carbonyl azide
  参考文献：
  名称：

  Asymmetric Synthesis of (1'S,2'R)-Cyclopropyl Carbocyclic Nucleosides

  摘要：

  Enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been accomplished. The key intermediates 7 and 9 were synthesized from D-glyceraldehyde acetonide 1, which was converted to the alpha,beta-unsaturated ester 2 and then reduced to give allylic alcohol 3a. Stereoselective construction of the cyclopropyl ring of 3a and 3b followed by oxidation gave acid 5, which was treated under Curtius rearrangement conditions to obtain the urea intermediate 7. The urea intermediate was utilized to prepare uracil 14, thymine 15, and cytosine 18 nucleosides. The purine derivatives were prepared from cyclopropylamine 9 by condensation with 4,6-dichloro-5-form-amidopyrimidine or 4,6-dichloro-2-aminopyrimidine.

  DOI：

  10.1021/jo00121a047

文献信息

• Synthesis of enantiomerically pure cyclopropyl carbocyclic nucleosides
  作者：Yufen Zhao、Te-Fang Yang、Migyoung Lee、Byoung K. Chun、Jinfa Du、Raymond F. Schinazi、Doowon Lee、M.Gary Newton、Chung K. Chu

  DOI：10.1016/s0040-4039(00)73511-8

  日期：1994.7

  The enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been achieved and the key intermediate was characterized by X-ray crystallography.

  已经实现了环丙基碳环核苷的对映体合成，并且通过X射线晶体学表征了关键中间体。