(1R,2S,5S,3R,4R)-1-(3-ethoxyacryloyl)carbamoylamino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane | 1069040-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,5S,3R,4R)-1-(3-ethoxyacryloyl)carbamoylamino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane
• CAS: 1069040-55-6
• 化学式: C₃₂H₄₂N₂O₆Si
• 分子量: 578.781
• InChiKey: PZQHLZVSBSKNIE-SEGGDSSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.12
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,5S,3R,4R)-1-(3-ethoxyacryloyl)carbamoylamino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以21%的产率得到1-[(1R,2S,5S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)bicyclo[3.1.0]hex-1-yl]-1,3-dihydropyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure (S)-Methanocarbaribo Uracil Nucleoside Derivatives for Use as Antiviral Agents and P2Y Receptor Ligands

  摘要：

  We have developed an approach toward enantiomerically pure (S)-methanocarba ribonucleosides based on several functional group transformations on a sensitive bicyclo[3.1.0]-hexane system. D-Ribose was transformed into methanocarba alcohol 3 followed by conversion of the OH group to a nitrile with inversion of configuration at C4. The nitrile group was subsequently reduced in two stages to the 5'-hydroxymethyl group. An ester group appended to a tertiary carbon (Cl) was transformed to an amino group as a nucleobase precursor.

  DOI：

  10.1021/jo801224j
• 作为产物：
  描述：

  (1R,2S,5S,3R,4R)-1-amino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane 、 (E)-3-乙氧基丙烯酰异氰酸酯 以 二氯甲烷 为溶剂， 以74%的产率得到(1R,2S,5S,3R,4R)-1-(3-ethoxyacryloyl)carbamoylamino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure (S)-Methanocarbaribo Uracil Nucleoside Derivatives for Use as Antiviral Agents and P2Y Receptor Ligands

  摘要：

  We have developed an approach toward enantiomerically pure (S)-methanocarba ribonucleosides based on several functional group transformations on a sensitive bicyclo[3.1.0]-hexane system. D-Ribose was transformed into methanocarba alcohol 3 followed by conversion of the OH group to a nitrile with inversion of configuration at C4. The nitrile group was subsequently reduced in two stages to the 5'-hydroxymethyl group. An ester group appended to a tertiary carbon (Cl) was transformed to an amino group as a nucleobase precursor.

  DOI：

  10.1021/jo801224j