(E)-1-[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-yl]-4-phenylbut-3-en-2-one | 152965-14-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (E)-1-[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-yl]-4-phenylbut-3-en-2-one
• CAS: 152965-14-5
• 化学式: C₃₂H₄₉N₅O₄Si₂
• 分子量: 623.943
• InChiKey: MLGAHONHHLITFA-GOUOBPCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-1-[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-yl]-4-phenylbut-3-en-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以91%的产率得到1-[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-yl]-4-phenylbutan-2-one
  参考文献：
  名称：

  Synthesis of nucleoside 3'-alkylphosphonates: intermediates for assembly of carbon-bridge dinucleotide analogs

  摘要：

  Several 3'-modified nucleosides have been prepared, through an initial Wittig or Horner-Wadsworth-Emmons condensation with an adenosine 3'-ketone, followed by catalytic hydrogenation of the resulting olefin. Subsequent reaction of the 3'alpha-methylene carboxylate with the lithium salt of diethyl ethylphosphonate gave a beta-keto phosphonate, while reaction of the methylene carboxylate with LDA, diethyl chlorophosphite, and O2 gives the corresponding alpha-phosphono ester. These new nucleoside phosphonates can be viewed as analogues of natural phosphates and also can serve as synthetic intermediates for preparation of carbon-bridged dinucleotide analogues. To give the first such example, the beta-keto phosphonate 13 was allowed to react with a nucleoside 5-aldehyde, affording the dinucleoside enone 23.

  DOI：

  10.1021/jo00079a027
• 作为产物：
  描述：

  9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 在 palladium on activated charcoal 正丁基锂 、 18-冠醚-6 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 82.67h， 生成 (E)-1-[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-yl]-4-phenylbut-3-en-2-one
  参考文献：
  名称：

  Synthesis of nucleoside 3'-alkylphosphonates: intermediates for assembly of carbon-bridge dinucleotide analogs

  摘要：

  Several 3'-modified nucleosides have been prepared, through an initial Wittig or Horner-Wadsworth-Emmons condensation with an adenosine 3'-ketone, followed by catalytic hydrogenation of the resulting olefin. Subsequent reaction of the 3'alpha-methylene carboxylate with the lithium salt of diethyl ethylphosphonate gave a beta-keto phosphonate, while reaction of the methylene carboxylate with LDA, diethyl chlorophosphite, and O2 gives the corresponding alpha-phosphono ester. These new nucleoside phosphonates can be viewed as analogues of natural phosphates and also can serve as synthetic intermediates for preparation of carbon-bridged dinucleotide analogues. To give the first such example, the beta-keto phosphonate 13 was allowed to react with a nucleoside 5-aldehyde, affording the dinucleoside enone 23.

  DOI：

  10.1021/jo00079a027

文献信息

• Synthesis of nucleoside 3'-alkylphosphonates: intermediates for assembly of carbon-bridge dinucleotide analogs
  作者：Koo Lee、David F. Wiemer

  DOI：10.1021/jo00079a027

  日期：1993.12

  Several 3'-modified nucleosides have been prepared, through an initial Wittig or Horner-Wadsworth-Emmons condensation with an adenosine 3'-ketone, followed by catalytic hydrogenation of the resulting olefin. Subsequent reaction of the 3'alpha-methylene carboxylate with the lithium salt of diethyl ethylphosphonate gave a beta-keto phosphonate, while reaction of the methylene carboxylate with LDA, diethyl chlorophosphite, and O2 gives the corresponding alpha-phosphono ester. These new nucleoside phosphonates can be viewed as analogues of natural phosphates and also can serve as synthetic intermediates for preparation of carbon-bridged dinucleotide analogues. To give the first such example, the beta-keto phosphonate 13 was allowed to react with a nucleoside 5-aldehyde, affording the dinucleoside enone 23.