(-)-(2E)-(4R,5R,6R)-5-Benzyloxy-4,6-dihydroxy-7-(1',3'-dithiolan-2'-yl)hept-2-enoate | 145741-65-7

• 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: (-)-(2E)-(4R,5R,6R)-5-Benzyloxy-4,6-dihydroxy-7-(1',3'-dithiolan-2'-yl)hept-2-enoate
• 英文别名: ethyl (E,4R,5R,6R)-6-(1,3-dithiolan-2-yl)-4,6-dihydroxy-5-phenylmethoxyhex-2-enoate
• CAS: 145741-65-7
• 化学式: C₁₈H₂₄O₅S₂
• 分子量: 384.518
• InChiKey: QPZUUSGIRXKIJG-MWXOSNHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-(2E)-(4R,5R,6R)-5-Benzyloxy-4,6-dihydroxy-7-(1',3'-dithiolan-2'-yl)hept-2-enoate 在 palladium on activated charcoal 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 二异丁基氢化铝 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 126.0h， 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：

  1,2-乙二硫醇 、 (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 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以68%的产率得到(-)-(2E)-(4R,5R,6R)-5-Benzyloxy-4,6-dihydroxy-7-(1',3'-dithiolan-2'-yl)hept-2-enoate
  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.