[(2R,3R,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-chlorooxolan-2-yl]methyl 2,2-dimethylpropanoate | 153864-70-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2R,3R,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-chlorooxolan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 153864-70-1
• 化学式: C₁₅H₂₂ClN₃O₄
• 分子量: 343.81
• InChiKey: KORFRGBLMYMMMU-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2R,3R,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-chlorooxolan-2-yl]methyl 2,2-dimethylpropanoate 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 以87%的产率得到2',3'-didehydro-2',3'-dideoxy-5-methylcytidine
  参考文献：
  名称：

  Improved Synthesis of 2′,3′-Dideoxycytidine (d2C) and Its Correlated Nucleoside Analogues

  摘要：

  2',3'-dideoxy- and 2',3'-dideoxy-2',3'-didehydrocytidine (d2C and d4C) have been synthesized in good yields from 2'-deoxyuridine via dichlorinated derivatives 7a-b. The same synthetic strategy was used in the synthesis of d2C(Me) and d4C(Me) from thymidine. Following this method the evaluable 3'-chloro-2'-deoxycytidine derivatives 9 - 12 can easily be obtained.

  DOI：

  10.1080/07328319308018568
• 作为产物：
  描述：

  2'-deoxy-5'-O-pivaloylthymidine 在 四氯化碳 、 氨 、 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 [(2R,3R,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-chlorooxolan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Improved Synthesis of 2′,3′-Dideoxycytidine (d2C) and Its Correlated Nucleoside Analogues

  摘要：

  2',3'-dideoxy- and 2',3'-dideoxy-2',3'-didehydrocytidine (d2C and d4C) have been synthesized in good yields from 2'-deoxyuridine via dichlorinated derivatives 7a-b. The same synthetic strategy was used in the synthesis of d2C(Me) and d4C(Me) from thymidine. Following this method the evaluable 3'-chloro-2'-deoxycytidine derivatives 9 - 12 can easily be obtained.

  DOI：

  10.1080/07328319308018568

文献信息

• Improved Synthesis of 2′,3′-Dideoxycytidine (d2C) and Its Correlated Nucleoside Analogues
  作者：L. De Napoli、A. Messere、D. Montesarchio、G. Piccialli、C. Santacroce

  DOI：10.1080/07328319308018568

  日期：1993.11

  2',3'-dideoxy- and 2',3'-dideoxy-2',3'-didehydrocytidine (d2C and d4C) have been synthesized in good yields from 2'-deoxyuridine via dichlorinated derivatives 7a-b. The same synthetic strategy was used in the synthesis of d2C(Me) and d4C(Me) from thymidine. Following this method the evaluable 3'-chloro-2'-deoxycytidine derivatives 9 - 12 can easily be obtained.