5-piperidinomethyluridine

• 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: 5-piperidinomethyluridine
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(piperidin-1-ylmethyl)pyrimidine-2,4-dione
• 化学式: C₁₅H₂₃N₃O₆
• 分子量: 341.364
• InChiKey: YXRQIQDDSPMRAK-HKUMRIAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-piperidinomethyluridine 生成 胸腺嘧啶
  参考文献：
  名称：

  IKOMA, JOSIXARU;XIGUTI, SIGEHKI

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(羟甲基)-2',3'-O-(异丙亚基)尿苷 在 吡啶 、 溶剂黄146 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 38.5h， 生成 5-piperidinomethyluridine
  参考文献：
  名称：

  Synthesis of various substituted 5-methyluridines (xm 5 U) and 2-thiouridines (xm 5 s 2 U) via nucleophilic substitution of 5-pivaloyloxymethyluridine/2-thiouridine

  摘要：

  5-Pivaloyloxymethyluridine and its 2-thio analogue have been utilized as convenient substrates for the synthesis of various 5-methyluridines (xm(5)U) and 5-methyl-2-thiouridines (xm(5)s(2)U). The pivaloyloxy group (OPiv) located at the pseudobenzylic position was effectively substituted with a series of nucleophiles: ammonia, primary and secondary amines including secondary cyclic amines, tetrabutylammonium salts of amino acids, an alkoxide and a thiolate. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.023

文献信息

• IKOMA, JOSIXARU;XIGUTI, SIGEHKI
  作者：IKOMA, JOSIXARU、XIGUTI, SIGEHKI

  DOI：——

  日期：——
• JPS6363668A
  申请人：——

  公开号：JPS6363668A

  公开（公告）日：1988-03-22
• Synthesis of various substituted 5-methyluridines (xm 5 U) and 2-thiouridines (xm 5 s 2 U) via nucleophilic substitution of 5-pivaloyloxymethyluridine/2-thiouridine
  作者：Karolina Bartosik、Grazyna Leszczynska

  DOI：10.1016/j.tetlet.2015.10.023

  日期：2015.11

  5-Pivaloyloxymethyluridine and its 2-thio analogue have been utilized as convenient substrates for the synthesis of various 5-methyluridines (xm(5)U) and 5-methyl-2-thiouridines (xm(5)s(2)U). The pivaloyloxy group (OPiv) located at the pseudobenzylic position was effectively substituted with a series of nucleophiles: ammonia, primary and secondary amines including secondary cyclic amines, tetrabutylammonium salts of amino acids, an alkoxide and a thiolate. (C) 2015 Elsevier Ltd. All rights reserved.