(+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol | 145741-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol
• CAS: 145741-67-9
• 化学式: C₂₂H₃₆O₅Si
• 分子量: 408.61
• InChiKey: FSZGHAZDFWTQSI-JYRKZWEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol 在 palladium on activated charcoal 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 氢气 、 二异丁基氢化铝 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 68.0h， 生成 5-Deoxycarba-α-D-ribo-hexofuranose
  参考文献：
  名称：

  Radical cyclisation reactions leading to polyhydroxylated cyclopentane derivatives: synthesis of (1R,2R,3S,4R)- and (1S,2S,3R,4S)-4-hydroxyethylcyclopentane-1,2,3-triol

  摘要：

  The tetraol (-)-1 has been prepared from a derivative of (D)-allose 3. The stereoselective carbocyclization reaction (8 double line arrow pointing right 11) formed the key step in this sequence. The enantiomeric cyclopentane derivative(+)-1 was also prepared from compound 3.In this synthesis the cyclization of compound 18 to provide the carbocycle 19 features as the critical carbon-carbon bond forming reaction.

  DOI：

  10.1039/p19920002625
• 作为产物：
  描述：

  (Z)-3-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acrylic acid ethyl ester 在 咪唑 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 74.0h， 生成 (+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol
  参考文献：
  名称：

  Radical cyclisation reactions leading to polyhydroxylated cyclopentane derivatives: synthesis of (1R,2R,3S,4R)- and (1S,2S,3R,4S)-4-hydroxyethylcyclopentane-1,2,3-triol

  摘要：

  The tetraol (-)-1 has been prepared from a derivative of (D)-allose 3. The stereoselective carbocyclization reaction (8 double line arrow pointing right 11) formed the key step in this sequence. The enantiomeric cyclopentane derivative(+)-1 was also prepared from compound 3.In this synthesis the cyclization of compound 18 to provide the carbocycle 19 features as the critical carbon-carbon bond forming reaction.

  DOI：

  10.1039/p19920002625