2'-deoxy-2-S-methylthiouridine | 1268475-32-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2'-deoxy-2-S-methylthiouridine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-methylsulfanylpyrimidin-4-one
• CAS: 1268475-32-6
• 化学式: C₁₀H₁₄N₂O₄S
• 分子量: 258.298
• InChiKey: UAEQROPJCSRBAJ-LKEWCRSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2-S-methylthiouridine 在 一水合肼 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 1-(2-deoxy-β-D-ribofuranosyl)-2-hydrazinopyrimidin-4-one
  参考文献：
  名称：

  Synthesis and Photochemical Behavior of the Tetrazolo Tautomer of 2-Azido-4-pyrimidinone-2′-deoxyriboside

  摘要：

  The 2-azido analogue of 2'-deoxyuridine was prepared in three steps from 2'-deoxy-2-thiouridine. The sulfur atom of the 2-thio nucleoside was methylated and then displaced by hydrazine to furnish the corresponding 2-hydrazino derivative. After diazotization, the 2-azido compound that exists as its tetrazolo tautomer was obtained. Upon UV irradiation in aqueous solution, the title compound led to isocytosine.

  DOI：

  10.1021/jo102316r
• 作为产物：
  描述：

  2'-脱氧-5'-O-[(4-甲基苯基)磺酰基]尿苷 在 吡啶 、 硫化氢 、 碳酸氢钠 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 51.33h， 生成 2'-deoxy-2-S-methylthiouridine
  参考文献：
  名称：

  Synthesis and Photochemical Behavior of the Tetrazolo Tautomer of 2-Azido-4-pyrimidinone-2′-deoxyriboside

  摘要：

  The 2-azido analogue of 2'-deoxyuridine was prepared in three steps from 2'-deoxy-2-thiouridine. The sulfur atom of the 2-thio nucleoside was methylated and then displaced by hydrazine to furnish the corresponding 2-hydrazino derivative. After diazotization, the 2-azido compound that exists as its tetrazolo tautomer was obtained. Upon UV irradiation in aqueous solution, the title compound led to isocytosine.

  DOI：

  10.1021/jo102316r

文献信息

• Synthesis and Photochemical Behavior of the Tetrazolo Tautomer of 2-Azido-4-pyrimidinone-2′-deoxyriboside
  作者：Stéphanie Gourdain、Christian Petermann、Agathe Martinez、Dominique Harakat、Pascale Clivio

  DOI：10.1021/jo102316r

  日期：2011.3.18

  The 2-azido analogue of 2'-deoxyuridine was prepared in three steps from 2'-deoxy-2-thiouridine. The sulfur atom of the 2-thio nucleoside was methylated and then displaced by hydrazine to furnish the corresponding 2-hydrazino derivative. After diazotization, the 2-azido compound that exists as its tetrazolo tautomer was obtained. Upon UV irradiation in aqueous solution, the title compound led to isocytosine.