3,3'-N,O-diacetyl-5'-O-(prop-2-enyl)thymidine | 876403-41-7

• 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: 3,3'-N,O-diacetyl-5'-O-(prop-2-enyl)thymidine
• CAS: 876403-41-7
• 化学式: C₁₇H₂₂N₂O₇
• 分子量: 366.371
• InChiKey: UMRVKNFMIYLCAL-RRFJBIMHSA-N

物化性质

• 沸点：
  488.4±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105.83
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3,3'-N,O-diacetyl-5'-O-(prop-2-enyl)thymidine 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (Z)-1,4-bis-O-(3',3-N,O-diacetylthymidin-5'-yl)but-2-ene 、 (E)-1,4-bis-O-(3',3-N,O-diacetylthymidin-5'-yl)but-2-ene
  参考文献：
  名称：

  New Dinucleoside Analogues via Cross-Coupling Metathesis

  摘要：

  Synthesis of 3'-3', 5-5', and 3'-5' dimeric thymidine, linked by an olefinic chain between glycosidic moieties is described. Cross metathesis reaction of 3' or 5' O-allyl analogues of thymidine led to the expected 3'-3' and 5'-5' dimeric compounds, respectively. In order to obtain the 3'-5' dimer, 5'-O-allyl and 3'-O-allyl monomers were first linked by their free 3' OH and 5' OH groups through a glutaryl spacer; ring closing metathesis was then operated upon this temporary dimer, followed by glutaryl removal.

  DOI：

  10.1081/ncn-60595
• 作为产物：
  描述：

  beta-胸苷 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.09h， 生成 3,3'-N,O-diacetyl-5'-O-(prop-2-enyl)thymidine
  参考文献：
  名称：

  New Dinucleoside Analogues via Cross-Coupling Metathesis

  摘要：

  Synthesis of 3'-3', 5-5', and 3'-5' dimeric thymidine, linked by an olefinic chain between glycosidic moieties is described. Cross metathesis reaction of 3' or 5' O-allyl analogues of thymidine led to the expected 3'-3' and 5'-5' dimeric compounds, respectively. In order to obtain the 3'-5' dimer, 5'-O-allyl and 3'-O-allyl monomers were first linked by their free 3' OH and 5' OH groups through a glutaryl spacer; ring closing metathesis was then operated upon this temporary dimer, followed by glutaryl removal.

  DOI：

  10.1081/ncn-60595