sodium (3aS,4S,6R,6aR)-6-(6-benzamido-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate | 1581768-74-2

• 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: sodium (3aS,4S,6R,6aR)-6-(6-benzamido-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
• CAS: 1581768-74-2
• 化学式: C₂₀H₁₈N₅O₆*Na
• 分子量: 447.383
• InChiKey: ZNYMGLHJKKQLLI-NKOYCVERSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.75
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  140.52
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  sodium (3aS,4S,6R,6aR)-6-(6-benzamido-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate 在 吡啶 、 Ru[(S,S)-Tsdpen](p-cymene) 、 sodium formate 、 1-丙基磷酸酐 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 28.5h， 生成 N⁶-benzoyl-2',3'-O-isopropylidene-(5'S)-5'-C-methyladenosine
  参考文献：
  名称：

  Preparation of Both C5′ Epimers of 5′-C-Methyladenosine: Reagent Control Trumps Substrate Control

  摘要：

  Adenosine-derived ketone 5 was subjected to Noyori asymmetric transfer hydrogenation (ATH) using aqueous sodium formate as a stoichiometric reductant. Despite the well-known sensitivity of ATH to stereoelectronic effects from a contiguous stereogenic center, the 5' stereochemistry was overwhelmingly controlled by the chirality of the catalyst. Both the (5'S,4'R) and the (5'R,4'R) diastereomers could be prepared selectively in good yields. An efficient three-step route that provides ketone 5 in 75% overall yield was developed.

  DOI：

  10.1021/jo500089t
• 作为产物：
  描述：

  N6-苯甲酰基-2',3'-O-异丙亚基腺苷 在 2,2,6,6-四甲基哌啶氧化物 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 以87%的产率得到sodium (3aS,4S,6R,6aR)-6-(6-benzamido-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
  参考文献：
  名称：

  Preparation of Both C5′ Epimers of 5′-C-Methyladenosine: Reagent Control Trumps Substrate Control

  摘要：

  Adenosine-derived ketone 5 was subjected to Noyori asymmetric transfer hydrogenation (ATH) using aqueous sodium formate as a stoichiometric reductant. Despite the well-known sensitivity of ATH to stereoelectronic effects from a contiguous stereogenic center, the 5' stereochemistry was overwhelmingly controlled by the chirality of the catalyst. Both the (5'S,4'R) and the (5'R,4'R) diastereomers could be prepared selectively in good yields. An efficient three-step route that provides ketone 5 in 75% overall yield was developed.

  DOI：

  10.1021/jo500089t