2'-deoxy-2-O-ethyluridine | 66656-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2'-deoxy-2-O-ethyluridine
• 英文别名: 1-(β-D-erythro-2-deoxy-pentofuranosyl)-4-ethoxy-1H-pyrimidin-2-one；O²-Ethyldeoxyuridin；2-ethoxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-4-one
• CAS: 66656-47-1
• 化学式: C₁₁H₁₆N₂O₅
• 分子量: 256.258
• InChiKey: QOMJZZYOCMJURT-QXFUBDJGSA-N

物化性质

• 沸点：
  449.1±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)
• 溶解度：
  乙腈（微溶）；氯仿（微溶）、二氯甲烷（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2-O-ethyluridine 在 吡啶 、 硫化氢 作用下， 以74%的产率得到2-硫代2'-脱氧尿苷
  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：

  乙醇 、 2'-脱氧-5'-O-[(4-甲基苯基)磺酰基]尿苷 在 碳酸氢钠 作用下， 反应 48.0h， 以69%的产率得到2'-deoxy-2-O-ethyluridine
  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.