(+)-3-Benzyloxy-6-bromo-1,2-isopropylidenedioxy-6-deoxy-α-D-allofuranose | 145741-54-4

• 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: (+)-3-Benzyloxy-6-bromo-1,2-isopropylidenedioxy-6-deoxy-α-D-allofuranose
• 英文别名: (1S)-1-[(3aR,5R,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-bromoethanol
• CAS: 145741-54-4
• 化学式: C₁₆H₂₁BrO₅
• 分子量: 373.244
• InChiKey: XNTYWMXVEHTRFS-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-3-Benzyloxy-6-bromo-1,2-isopropylidenedioxy-6-deoxy-α-D-allofuranose 在 咪唑 、 4-二甲氨基吡啶 、 sodium periodate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 35.0h， 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
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 在 吡啶 、 四溴化碳 、 三苯基膦 作用下， 反应 0.15h， 以71%的产率得到(+)-3-Benzyloxy-6-bromo-1,2-isopropylidenedioxy-6-deoxy-α-D-allofuranose
  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.