5'-O-benzoyl-2',3'-dideoxy-3'-phenylselenothymidine | 170871-58-6

• 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'-O-benzoyl-2',3'-dideoxy-3'-phenylselenothymidine
• 英文别名: [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-phenylselanyloxolan-2-yl]methyl benzoate
• CAS: 170871-58-6
• 化学式: C₂₃H₂₂N₂O₅Se
• 分子量: 485.398
• InChiKey: PGUKSBRNOGDYMO-HSALFYBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-O-benzoyl-2',3'-dideoxy-3'-phenylselenothymidine 在 双氧水 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 司他夫定
  参考文献：
  名称：

  Efficient Transformation of Thymidine into 2′,3′-Didehydro-2′,3′-Dideoxy-Thymidine (D4T) Involving Opening of a 2,3′-Anhydro Derivative by Phenylselenol

  摘要：

  A new, high-yielding method for introduction of the selenophenyl residue at the 3'- position of thymidine is reported. This reaction avoided any strongly basic or reductive reagent, thus allowing the use of benzoate ester as a protective group at O-5'. Further oxidation-elimination sequence followed by basic deprotection afforded 2',3'-didehydro-2',3'-dideoxythymidine (D4T) in 67.5 % overall yield from thymidine.

  DOI：

  10.1080/15257779508010686
• 作为产物：
  描述：

  beta-胸苷 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 生成 5'-O-benzoyl-2',3'-dideoxy-3'-phenylselenothymidine
  参考文献：
  名称：

  Efficient Transformation of Thymidine into 2′,3′-Didehydro-2′,3′-Dideoxy-Thymidine (D4T) Involving Opening of a 2,3′-Anhydro Derivative by Phenylselenol

  摘要：

  A new, high-yielding method for introduction of the selenophenyl residue at the 3'- position of thymidine is reported. This reaction avoided any strongly basic or reductive reagent, thus allowing the use of benzoate ester as a protective group at O-5'. Further oxidation-elimination sequence followed by basic deprotection afforded 2',3'-didehydro-2',3'-dideoxythymidine (D4T) in 67.5 % overall yield from thymidine.

  DOI：

  10.1080/15257779508010686

文献信息

• Efficient Transformation of Thymidine into 2′,3′-Didehydro-2′,3′-Dideoxy-Thymidine (D4T) Involving Opening of a 2,3′-Anhydro Derivative by Phenylselenol
  作者：Stéfan Becouarn、Stanislas Czernecki、Jean-Marc Valéry

  DOI：10.1080/15257779508010686

  日期：1995.8

  A new, high-yielding method for introduction of the selenophenyl residue at the 3'- position of thymidine is reported. This reaction avoided any strongly basic or reductive reagent, thus allowing the use of benzoate ester as a protective group at O-5'. Further oxidation-elimination sequence followed by basic deprotection afforded 2',3'-didehydro-2',3'-dideoxythymidine (D4T) in 67.5 % overall yield from thymidine.