1<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>cytosine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>cytosine
• 英文别名: 4-amino-1-[[(3R,4S)-1-diethoxyphosphoryl-4-phenylmethoxypentan-3-yl]oxymethyl]pyrimidin-2-one
• 化学式: C₂₁H₃₂N₃O₆P
• 分子量: 453.475
• InChiKey: VPCWQSWTRVBBHS-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Diethyl (3R,4S)-4-(benzyloxy)-3-hydroxypentanephosphonate 在 盐酸 、 ammonium sulfate 、 四乙基碘化铵 、 六甲基二硅氮烷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>cytosine
  参考文献：
  名称：

  Synthesis of Phosphonate Isosteres of 2‘-Deoxy-1‘,2‘-seco-nucleotides

  摘要：

  Practical and convergent syntheses of 2'-deoxy-1',2'-seco-nucleophosphonates and 1',2'-seco-nucleophosphonates are described. Phosphonate chirons derived from D-isoascorbic acid were used in alkylation of functionalized nucleobases to provide the title phosphonate isosteres in good yields. Subsequent deprotection and deesterification led to the 5'-C-methylenephosphonic acids which were conveniently purified using gravity flow C-18 reverse phase column chromatography.

  DOI：

  10.1021/jo951701v

文献信息

• Synthesis of Phosphonate Isosteres of 2‘-Deoxy-1‘,2‘-seco-nucleotides
  作者：Hussein I. El-Subbagh、Saibaba Racha、Elie Abushanab、Raymond P. Panzica

  DOI：10.1021/jo951701v

  日期：1996.1.1

  Practical and convergent syntheses of 2'-deoxy-1',2'-seco-nucleophosphonates and 1',2'-seco-nucleophosphonates are described. Phosphonate chirons derived from D-isoascorbic acid were used in alkylation of functionalized nucleobases to provide the title phosphonate isosteres in good yields. Subsequent deprotection and deesterification led to the 5'-C-methylenephosphonic acids which were conveniently purified using gravity flow C-18 reverse phase column chromatography.