(2R,3S,4S)-2-Benzyloxy-5-bromo-4-(tert-butyldiphenylsilyloxy)-3-formyloxypentanal | 145741-58-8

• 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: (2R,3S,4S)-2-Benzyloxy-5-bromo-4-(tert-butyldiphenylsilyloxy)-3-formyloxypentanal
• 英文别名: [(2S,3S,4R)-1-bromo-2-[tert-butyl(diphenyl)silyl]oxy-5-oxo-4-phenylmethoxypentan-3-yl] formate
• CAS: 145741-58-8
• 化学式: C₂₉H₃₃BrO₅Si
• 分子量: 569.568
• InChiKey: YCNOODLWVYMFBR-OZNIXHKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-2-Benzyloxy-5-bromo-4-(tert-butyldiphenylsilyloxy)-3-formyloxypentanal 在 偶氮二异丁腈 、 三正丁基氢锡 、 苯甲酸 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 (1R,2R,3S,4S)-3-Benzyloxy-1-tert-butyldiphenylsilyloxy-4-ethoxycarbonylmethyl-2-formyloxycyclopentane
  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：

  3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium periodate 、 四溴化碳 、 溶剂黄146 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 35.15h， 生成 (2R,3S,4S)-2-Benzyloxy-5-bromo-4-(tert-butyldiphenylsilyloxy)-3-formyloxypentanal
  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

文献信息

• 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
  作者：Stanley M. Roberts、Karoline A. Shoberu

  DOI：10.1039/p19920002625

  日期：——

  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.