thymidine 5'-O-(1,1-dithiotriphosphate) | 132298-05-6

• 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: thymidine 5'-O-(1,1-dithiotriphosphate)
• 英文别名: [[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-sulfanylphosphinothioyl] phosphono hydrogen phosphate
• CAS: 132298-05-6
• 化学式: C₁₀H₁₇N₂O₁₂P₃S₂
• 分子量: 514.304
• InChiKey: NYTFMONJWJOSBY-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  235
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  3'-O-acetylthymidine 在 吡啶 、 ammonium hydroxide 、 三正丁胺 、 三丁基焦磷酸铵 、 sulfur 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 thymidine 5'-O-(1,1-dithiotriphosphate)
  参考文献：
  名称：

  Synthesis of nucleoside 5'-O-(1,3-dithiotriphosphates) and 5'-O-(1,1-dithiotriphosphates)

  摘要：

  The synthesis of 3'-deoxy-3'-azidothymidine 5'-O-(1,3-dithiotriphosphate) (5) as the first example of a nucleoside 5'-O-(1,3-dithiotriphosphate) is described. 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one phosphitylates the 5'-hydroxy group of 3'deoxy-3'-azidothymidine to form intermediate 1. Reaction of 1 with thiopyrophosphate (9) and sulfur results in the formation of an unseparable mixture of 3'-deoxy-3'-azidothymidine 5'-O-(1,3-dithiotriphosphate) (5) and 3'-deoxy-3'-azidothymidine 5'-O-(1,2-dithiotriphosphate) (3). Selective hydrolysis of 5 allows isolation of 3. However, reaction of 1 with P1-O-(cyanoethyl)-P1-thiopyrophosphate (8) and sulfur produced the diastereomers of 5 in good yield. Compound 8 is prepared by reaction of 3-hydroxyproprionitrile with 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one, pyrophosphate, and sulfur to yield 10, which is ring opened to 8 by reaction with ethylenediamine. Hydrolysis of this compound leads to 9. An alternative route to nucleoside 5'-O-(1,3-dithiotriphosphates) consists of reacting a nucleoside 5'-O-(1-thiocyclotriphosphate) such as 13 with Li2S. This reaction, when performed in pyridine/dioxane, leads to a mixture of the nucleoside 5'-O-(1,3-dithiotriphosphate) and the nucleoside 5'-O-(1,1-dithiotriphosphate). The latter is the only nucleotide product when the reaction is carried out in DMF.

  DOI：

  10.1021/jo00005a023

文献信息

• The Synthesis of Nucleoside 5'-O-(1,1-Dithiotriphosphates)
  作者：Andrzej Okruszek、Magdalena Olesiak、Jan Balzarini

  DOI：10.1021/jm00048a021

  日期：1994.10

  Appropriately protected nucleoside 5'-O-(2-thio-1,3,2-dithiaphospholanes) react with inorganic pyrophosphate in the presence of a strong base catalyst (DBU) to give nucleoside 5'-O-(1,1-dithiotriphosphates) 1a-g. The latter compounds, including an AZT analogue, show modest antivirial activity against HIV-1 and HTV-8 replication in CEM cells. The AZT and deoxyadenosine derivatives were found to be inhibitors of HIV reverse transcriptase.