(2S,3S)-1,4-bis(benzyloxy)-2,3-bis(2,3-epoxypropyloxy)butane | 679399-13-4

• 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: (2S,3S)-1,4-bis(benzyloxy)-2,3-bis(2,3-epoxypropyloxy)butane
• 英文别名: (2s,3s)-1,4-Dibenzyloxy-2,3-bis(2-oxiranylmethoxy)butane；2-[[(2S,3S)-3-(oxiran-2-ylmethoxy)-1,4-bis(phenylmethoxy)butan-2-yl]oxymethyl]oxirane
• CAS: 679399-13-4
• 化学式: C₂₄H₃₀O₆
• 分子量: 414.499
• InChiKey: KINJUAFRFNXSRH-MXXWWZHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-1,4-bis(benzyloxy)-2,3-bis(2,3-epoxypropyloxy)butane 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 (2S,3S)-2,3-bis(hydroxymethyl)-1,4-dioxa-8,11-diazacyclotetradecane-6,13-diol
  参考文献：
  名称：

  具有环外羟基的手性氮杂冠醚的合成及其在四氢硼酸钠中不对称还原酮的应用

  摘要：

  New chiral diaza crown ethers with exocyclic hydroxy groups were synthesized by reactions of (2S,3S)-1,4-dibenzyloxy-2,3-bis(2-oxiranylmethoxy)butane with N,N'-dibenzyl-1,2-ethanediamine and (4S,5S)-4,5-bis(benzylaminomethyl)-2,2-dimethyl-1,3-dioxolane. Catalytic debenzylation of the products gave the corresponding derivatives having secondary amino groups. The obtained diaza crown ethers, as well as some known crown ethers, were used as asymmetric catalysts in the reduction of pinacolone and acetophenone with sodium tetrahydridoborate in methylene chloride. Depending on the catalyst structure, the optical yield of the reduction products ranged from 5 to 90%.

  DOI：

  10.1023/b:rujo.0000003201.57627.ee
• 作为产物：
  描述：

  (-)-1,4-O-二苯基-L-苏醇 、 环氧氯丙烷 在 sodium hydroxide 、 Bu₄N*H₂SO₄ 、 水 作用下， 反应 1.5h， 以68%的产率得到(2S,3S)-1,4-bis(benzyloxy)-2,3-bis(2,3-epoxypropyloxy)butane
  参考文献：
  名称：

  具有环外羟基的手性氮杂冠醚的合成及其在四氢硼酸钠中不对称还原酮的应用

  摘要：

  New chiral diaza crown ethers with exocyclic hydroxy groups were synthesized by reactions of (2S,3S)-1,4-dibenzyloxy-2,3-bis(2-oxiranylmethoxy)butane with N,N'-dibenzyl-1,2-ethanediamine and (4S,5S)-4,5-bis(benzylaminomethyl)-2,2-dimethyl-1,3-dioxolane. Catalytic debenzylation of the products gave the corresponding derivatives having secondary amino groups. The obtained diaza crown ethers, as well as some known crown ethers, were used as asymmetric catalysts in the reduction of pinacolone and acetophenone with sodium tetrahydridoborate in methylene chloride. Depending on the catalyst structure, the optical yield of the reduction products ranged from 5 to 90%.

  DOI：

  10.1023/b:rujo.0000003201.57627.ee