9-<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>guanine | 174358-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>guanine
• 英文别名: 2-amino-9-[[(3R,4S)-1-diethoxyphosphoryl-4-phenylmethoxypentan-3-yl]oxymethyl]-1H-purin-6-one
• CAS: 174358-91-9
• 化学式: C₂₂H₃₂N₅O₆P
• 分子量: 493.5
• InChiKey: YRQAGSWHJIMGTA-FUHWJXTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>guanine 在 palladium dihydroxide 、 乙醇 、 环己烯 作用下， 反应 12.0h， 以80%的产率得到1-<<1-(diethylphosphonyl)-4(S)-hydroxy-3(R)-pentoxy>methyl>guanine
  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
• 作为产物：
  描述：

  O-6-苄基鸟嘌呤 在 palladium dihydroxide 、 乙醇 、 sodium hydride 、 环己烯 作用下， 反应 20.5h， 生成 9-<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>guanine
  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.