5-<3-(Trifluoroacetamido)-1-thiapropyl>-2'-deoxycytidine | 135638-74-3

• 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: 5-<3-(Trifluoroacetamido)-1-thiapropyl>-2'-deoxycytidine
• 英文别名: 5-[3-(Trifluoroacetamido)-1-thiapropyl]-2'-deoxycytidine；N-[2-[4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-5-yl]sulfanylethyl]-2,2,2-trifluoroacetamide
• CAS: 135638-74-3
• 化学式: C₁₃H₁₇F₃N₄O₅S
• 分子量: 398.363
• InChiKey: GKAIARDECJDMKA-LKEWCRSYSA-N

物化性质

• 密度：
  1.76±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.76
• 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：
  0.62
• 拓扑面积：
  139.7
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  5'-chloromercuri-2'-deoxycytidine 、 N,N'-Bis(trifluoroacetyl)cystamine 在 lithium tetrachloropalladate 作用下， 以 甲醇 为溶剂， 以5%的产率得到5-<3-(Trifluoroacetamido)-1-thiapropyl>-2'-deoxycytidine
  参考文献：
  名称：

  Palladium-mediated synthesis of C-5 pyrimidine nucleoside thioethers from disulfides and mercurinucleosides

  摘要：

  Thioether-linked side chains can be created at C-5 of pyrimidine nucleosides via a palladium-mediated reaction of mercurated nucleosides with organic disulfides. 5-(Chloromercuri)-2'-deoxyuridine reacts with butyl disulfide, phenyl disulfide, dimethyl 3,3'-dithiodipropionate, and N,N'-bis(trifluoroacetyl)cystamine to yield respectively 5-(1-thiapentyl)-2'-deoxyuridine, 5-(phenylthio)-2'-deoxyuridine, 5-[3-(methoxycarbonyl)-1-thiapropyl]-2'-deoxyuridine, and 5-[3-(trifluoroacetamido)-1-thiapropyl]-2'-deoxyuridine in yields ranging from 46 to 73%. Other mercurated nucleosides, including 5-(chloromercuri)-2'-deoxycytidine, 5-(chloromercuri)cytidine, and 5-(chloromercuri)tubercidin react with N,N'-bis(trifluoroacetyl)cystamine and lithium-palladium chloride in methanol to yield the corresponding coupled products, but the yields are much lower (5-10%). The nucleoside coupling reaction is complicated by competing side reactions between disulfides and Pd2+, which remain to be elucidated.

  DOI：

  10.1021/jo00019a025