(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-(hydroxymethyl)oxolan-2-one | 189160-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-(hydroxymethyl)oxolan-2-one
• CAS: 189160-26-7
• 化学式: C₁₂H₂₄O₄Si
• 分子量: 260.406
• InChiKey: FLUGTLUOYDZOAN-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-(hydroxymethyl)oxolan-2-one 在 咪唑 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of Novel L-Series 2′, 3′-Dideoxy-3′-Hydroxy-Methyl-Nucleosides and a Convenient Method for the Separation of Nucleosede Anomers

  摘要：

  Photoinduced addition of methanol to S(R)-(tert-butyldimethylsilyloxymethyl)-2(5H)-furan-2-one (derived from L-gulono-1,4-lactone) provided the photoadduct 5 (R)-(tert-butyldimethylsiloxymethyl)-4(S)-hydroxymethyl-tetrahydrofuran-2-one, which was converted into two L-series-2',3'-dideoxy-3'-hydroxymethyl-nucleosides. In addition, we describe a new method for the chromatographic separation of cytidine anomers using a N-2-(4-nitrophenyl)ethyl carbamate derivative.

  DOI：

  10.1080/07328319708002533
• 作为产物：
  描述：

  甲醇 、 二苯甲酮 、 (2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2H-furan-5-one 以6%的产率得到
  参考文献：
  名称：

  Synthesis of Novel L-Series 2′, 3′-Dideoxy-3′-Hydroxy-Methyl-Nucleosides and a Convenient Method for the Separation of Nucleosede Anomers

  摘要：

  Photoinduced addition of methanol to S(R)-(tert-butyldimethylsilyloxymethyl)-2(5H)-furan-2-one (derived from L-gulono-1,4-lactone) provided the photoadduct 5 (R)-(tert-butyldimethylsiloxymethyl)-4(S)-hydroxymethyl-tetrahydrofuran-2-one, which was converted into two L-series-2',3'-dideoxy-3'-hydroxymethyl-nucleosides. In addition, we describe a new method for the chromatographic separation of cytidine anomers using a N-2-(4-nitrophenyl)ethyl carbamate derivative.

  DOI：

  10.1080/07328319708002533