2',3'-dideoxy-5'-O-ethoxycarbonyladenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3'-dideoxy-5'-O-ethoxycarbonyladenosine
• 英文别名: [(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl ethyl carbonate
• 化学式: C₁₃H₁₇N₅O₄
• 分子量: 307.309
• InChiKey: TYGZWPFUCUBJPS-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  氯甲酸乙酯 、 2',3'-dideoxy-5'-O-ethoxycarbonyladenosine 在 N-甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到[(2S,5R)-5-[6-(ethoxycarbonylamino)purin-9-yl]oxolan-2-yl]methyl ethyl carbonate
  参考文献：
  名称：

  Ether, Carbonate and Urethane Deoxynucleoside Derivatives as Prodrugs.

  摘要：

  3'-Deoxythymidine and its 3'-azido derivative, 2',3'-dideoxycytidine, 2',3'-dideoxyinosine and 2',3'-dideoxyadenosine have been acylated to form carbonates and methanes in chemoselective reactions. The nucleosides have been N- and/or O-alkylated by alpha-chloroethyl or chloromethyl alkyl carbonates to form alpha-alkyloxycarbonyloxyethyl or alkyloxycarbonyloxymethyl derivatives. The products are lipophilic in order to facilitate transport through biological membranes and are designed to be cleaved by esterases with liberation of the bioactive nucleoside. Initial esterase cleavage of the alkylated derivatives produces hemiacetals or -aminals which subsequently dissociate to the active nucleoside.

  DOI：

  10.3891/acta.chem.scand.50-0609
• 作为产物：
  描述：

  2',3'-双脱氧腺苷 、 焦碳酸二乙酯 在 4-二甲氨基吡啶 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 以49%的产率得到2',3'-dideoxy-5'-O-ethoxycarbonyladenosine
  参考文献：
  名称：

  Ether, Carbonate and Urethane Deoxynucleoside Derivatives as Prodrugs.

  摘要：

  3'-Deoxythymidine and its 3'-azido derivative, 2',3'-dideoxycytidine, 2',3'-dideoxyinosine and 2',3'-dideoxyadenosine have been acylated to form carbonates and methanes in chemoselective reactions. The nucleosides have been N- and/or O-alkylated by alpha-chloroethyl or chloromethyl alkyl carbonates to form alpha-alkyloxycarbonyloxyethyl or alkyloxycarbonyloxymethyl derivatives. The products are lipophilic in order to facilitate transport through biological membranes and are designed to be cleaved by esterases with liberation of the bioactive nucleoside. Initial esterase cleavage of the alkylated derivatives produces hemiacetals or -aminals which subsequently dissociate to the active nucleoside.

  DOI：

  10.3891/acta.chem.scand.50-0609

文献信息

• Ether, Carbonate and Urethane Deoxynucleoside Derivatives as Prodrugs.
  作者：Kristin Hammer、Jostein Hatlelid、Morten Grøtli、Joseph Arukwe、Jo Klaveness、Frode Rise、Kjell Undheim、Connie N. Rosendahl、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0609

  日期：——

  3'-Deoxythymidine and its 3'-azido derivative, 2',3'-dideoxycytidine, 2',3'-dideoxyinosine and 2',3'-dideoxyadenosine have been acylated to form carbonates and methanes in chemoselective reactions. The nucleosides have been N- and/or O-alkylated by alpha-chloroethyl or chloromethyl alkyl carbonates to form alpha-alkyloxycarbonyloxyethyl or alkyloxycarbonyloxymethyl derivatives. The products are lipophilic in order to facilitate transport through biological membranes and are designed to be cleaved by esterases with liberation of the bioactive nucleoside. Initial esterase cleavage of the alkylated derivatives produces hemiacetals or -aminals which subsequently dissociate to the active nucleoside.