2'-deoxy-5-methylcytidine-5'-dichlorophosphoridate | 1453266-28-8

• 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: 2'-deoxy-5-methylcytidine-5'-dichlorophosphoridate
• CAS: 1453266-28-8
• 化学式: C₁₀H₁₄Cl₂N₃O₅P
• 分子量: 358.118
• InChiKey: USQMWOSKQLWEJP-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  116.67
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2'-deoxy-5-methylcytidine-5'-dichlorophosphoridate 在 三正丁胺 、 三丁基焦磷酸铵 、 sodium perchlorate 作用下， 以 乙腈 、 丙酮 为溶剂， 反应 0.33h， 以7.60 g的产率得到tetrasodium 2'-deoxy-5-methylcytidine-5'-triphosphate
  参考文献：
  名称：

  Concise synthesis of 5-methyl-, 5-formyl, and 5-carboxy analogues of 2′-deoxycytidine-5′-triphosphate

  摘要：

  We describe a concise and efficient synthesis of 5-methyl-, 5-formyl-, and 5-carboxy-analogues of 2'-deoxycytidine-5'-triphosphate which are well known for their various biological applications. A protection-free one-pot synthesis was used to convert 5-methyl-2'-deoxycytidine into 5-methyl-2'-deoxycytidine-5'-triphosphate in high yield. 5-Formyl-2'-deoxycytidine-5'-triphosphate was obtained upon photosensitized oxidation (UV-A irradiation, lambda similar to 365 nm) of an aerated aqueous solution of 5-methyl-2'-deoxycytidine-5'-triphosphate with the use of menadione as the photosensitizer. 5-Formyl-2'-deoxycytidine-5'-triphosphate was converted into 5-carboxy-2'-deoxycytidine-5'-triphosphate by using biphasic TEMPO/BAIB oxidation method in high yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.102
• 作为产物：
  描述：

  5-甲基-2'-脱氧胞苷 在 磷酸三甲酯 、 三正丁胺 、 三氯氧磷 作用下， 反应 0.97h， 生成 2'-deoxy-5-methylcytidine-5'-dichlorophosphoridate
  参考文献：
  名称：

  Concise synthesis of 5-methyl-, 5-formyl, and 5-carboxy analogues of 2′-deoxycytidine-5′-triphosphate

  摘要：

  We describe a concise and efficient synthesis of 5-methyl-, 5-formyl-, and 5-carboxy-analogues of 2'-deoxycytidine-5'-triphosphate which are well known for their various biological applications. A protection-free one-pot synthesis was used to convert 5-methyl-2'-deoxycytidine into 5-methyl-2'-deoxycytidine-5'-triphosphate in high yield. 5-Formyl-2'-deoxycytidine-5'-triphosphate was obtained upon photosensitized oxidation (UV-A irradiation, lambda similar to 365 nm) of an aerated aqueous solution of 5-methyl-2'-deoxycytidine-5'-triphosphate with the use of menadione as the photosensitizer. 5-Formyl-2'-deoxycytidine-5'-triphosphate was converted into 5-carboxy-2'-deoxycytidine-5'-triphosphate by using biphasic TEMPO/BAIB oxidation method in high yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.102