3'-azido-3'-deoxy-5'-O-diethylcarbamoylthymidine

• 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'-azido-3'-deoxy-5'-O-diethylcarbamoylthymidine
• 英文别名: [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl N,N-diethylcarbamate
• 化学式: C₁₅H₂₂N₆O₅
• 分子量: 366.377
• InChiKey: XNRFGTTUBDXOEZ-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  齐多夫定	3'-azido-2',3'-deoxythymidine	30516-87-1	C10H13N5O4	267.244

反应信息

• 作为反应物：
  描述：

  1-氯乙基乙基碳酸酯 、 3'-azido-3'-deoxy-5'-O-diethylcarbamoylthymidine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以55%的产率得到Carbonic acid 1-[3-((2R,4S,5S)-4-azido-5-diethylcarbamoyloxymethyl-tetrahydro-furan-2-yl)-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-ethyl ester ethyl ester
  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：

  齐多夫定 、 N,N-二乙基氯甲酰胺 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以95%的产率得到3'-azido-3'-deoxy-5'-O-diethylcarbamoylthymidine
  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.