((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-chlorotetrahydrofuran-2-yl)methyl pivalate | 153864-69-8

• 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,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-chlorotetrahydrofuran-2-yl)methyl pivalate
• CAS: 153864-69-8
• 化学式: C₁₄H₂₀ClN₃O₄
• 分子量: 329.783
• InChiKey: QFFSEMDZEGPVOZ-IQJOONFLSA-N

物化性质

• 沸点：
  477.3±55.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  96.44
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-chlorotetrahydrofuran-2-yl)methyl pivalate 在 palladium on activated charcoal potassium tert-butylate 、 氢气 作用下， 以 乙醇 、 叔丁醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 2,3-二脱氧胞啶
  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：

  2,2-Dimethyl-propionic acid (2R,3S,5R)-3-chloro-5-(4-chloro-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 在 氨 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以31 mg的产率得到((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-chlorotetrahydrofuran-2-yl)methyl pivalate
  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