3'-azido-3'-deoxy-5'-thymidinyl 5'-uridinyl phosphate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （5'->5'）-二核苷酸
• 英文名称: 3'-azido-3'-deoxy-5'-thymidinyl 5'-uridinyl phosphate
• 英文别名: [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• 化学式: C₁₉H₂₄N₇O₁₂P
• 分子量: 573.413
• InChiKey: JROSSZFYXGPGLZ-KEMHXHKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  228
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  齐多夫定 、 尿嘧啶核苷 在 四氮唑 、 acetamidomethyl NovaGel^TM-2-iPr₂N-1,3,2-oxathiaphospholane 、 叔丁基过氧化氢 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二甲基亚砜 、 癸烷 为溶剂， 反应 40.0h， 以61%的产率得到3'-azido-3'-deoxy-5'-thymidinyl 5'-uridinyl phosphate
  参考文献：
  名称：

  Solid-Phase Synthesis of Dinucleoside and Nucleoside-Carbohydrate Phosphodiesters and Thiophosphodiesters

  摘要：

  Unprotected nucleosides (ROH) were reacted with two polymers bound to N, N-diisopropylamino- 1,3,2-oxathiaphospholane in the presence of 1H-terazole. Oxidation with tertbutyl hydroperoxide or sulfurization with Beaucage's reagent, followed by the 1,3,2-oxathiaphospholane ring opening with unprotected nucleosides or carbohydrates (R'OH) in the presence of DBU, afforded nucleoside-(5'-5')-nucleoside or nucleoside- carbohydrate phosphodiester and thiophosphodiester derivatives through the elimination of polymer-bound ethylene episulfide. This strategy offers the advantages of facile isolation of final products and monosubstitution of unprotected nucleosides and carbohydrates.

  DOI：

  10.1021/jo0611115

文献信息

• Solid-Phase Synthesis of Dinucleoside and Nucleoside-Carbohydrate Phosphodiesters and Thiophosphodiesters
  作者：Yousef Ahmadibeni、Keykavous Parang

  DOI：10.1021/jo0611115

  日期：2006.8.1

  Unprotected nucleosides (ROH) were reacted with two polymers bound to N, N-diisopropylamino- 1,3,2-oxathiaphospholane in the presence of 1H-terazole. Oxidation with tertbutyl hydroperoxide or sulfurization with Beaucage's reagent, followed by the 1,3,2-oxathiaphospholane ring opening with unprotected nucleosides or carbohydrates (R'OH) in the presence of DBU, afforded nucleoside-(5'-5')-nucleoside or nucleoside- carbohydrate phosphodiester and thiophosphodiester derivatives through the elimination of polymer-bound ethylene episulfide. This strategy offers the advantages of facile isolation of final products and monosubstitution of unprotected nucleosides and carbohydrates.