1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione | 470699-96-8

• 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: 1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS: 470699-96-8
• 化学式: C₁₇H₂₀N₂O₅
• 分子量: 332.356
• InChiKey: OGURBCHBHNRDJK-SOUVJXGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  93.55
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  氯磷酸二乙酯 、 1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以50%的产率得到5'α-O-benzyl-2'-deoxy-3'-O-diethylphosphorylthymidine
  参考文献：
  名称：

  The effect of the base in the fragmentation of nucleotide C4′ radicals

  摘要：

  A series of 3'-O-diethylphosphoryl-4'-alpha-[(2-halophenylethylthio)carbonyl] substituted esters of thymidine, cytidine, adenosine and guanosine are prepared by total synthesis and used as C4'-radical precursors in a competition kinetic method using tributyltin hydride as the reductant. The pseudo-first order rate constants for the C4'-radicals so generated decrease in the order guansoine>cytidine>adenosine>thymidine with that for guanosine being too rapid for determination by the present competition kinetic method. A (119)Sn NMR method is presented for estimation of the purity of tin hydride solutions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00557-4
• 作为产物：
  描述：

  5'-O-benzyl-4'α-carboxyl-2'-deoxythymidine 在 偶氮二异丁腈 、 三正丁基氢锡 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 1-((2R,4S,5S)-5-Benzyloxymethyl-4-hydroxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  The effect of the base in the fragmentation of nucleotide C4′ radicals

  摘要：

  A series of 3'-O-diethylphosphoryl-4'-alpha-[(2-halophenylethylthio)carbonyl] substituted esters of thymidine, cytidine, adenosine and guanosine are prepared by total synthesis and used as C4'-radical precursors in a competition kinetic method using tributyltin hydride as the reductant. The pseudo-first order rate constants for the C4'-radicals so generated decrease in the order guansoine>cytidine>adenosine>thymidine with that for guanosine being too rapid for determination by the present competition kinetic method. A (119)Sn NMR method is presented for estimation of the purity of tin hydride solutions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00557-4