(2S,6S)-1-tert-butyldimethylsilyloxy-4,8-dioxaundeca-10-ene-2,6-diol | 1452161-51-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2S,6S)-1-tert-butyldimethylsilyloxy-4,8-dioxaundeca-10-ene-2,6-diol
• CAS: 1452161-51-1
• 化学式: C₁₅H₃₂O₅Si
• 分子量: 320.502
• InChiKey: TVPUTODIXKNLQM-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  21.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,6S)-1-tert-butyldimethylsilyloxy-4,8-dioxaundeca-10-ene-2,6-diol 在 四丁基氟化铵 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 28.0h， 生成 (2R,6S)-2,6-dibenzyloxy-10,11-epoxy-4,8-dioxaundecan-1-ol
  参考文献：
  名称：

  Short and Stereocontrolled Cyclic Polyglycerols Synthesis Using BF3·OEt2 Mediated Intramolecular Epoxide-Opening Reaction

  摘要：

  We developed a new method for the stereocontrolled synthesis of cyclic oligoglycerols. Optically pure solketal and epichlorohydrin were coupled with allyl alcohol under aqueous basic conditions to construct a linear triglycerol skeleton. After subsequent steps, the epoxy alcohol (7) obtained was treated with a catalytic amount of BF3 center dot OEt2 in CH2Cl2 to produce in a high yield of the desired cyclic triglycerol through a regioselective, intramolecular epoxide ring-opening reaction.

  DOI：

  10.3987/com-12-s(n)67
• 作为产物：
  描述：

  (2S,6S)-1,2-O-isopropylidene-4,8-dioxaundeca-10-en-6-ol 在 4-二甲氨基吡啶 、 水 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 (2S,6S)-1-tert-butyldimethylsilyloxy-4,8-dioxaundeca-10-ene-2,6-diol
  参考文献：
  名称：

  Short and Stereocontrolled Cyclic Polyglycerols Synthesis Using BF3·OEt2 Mediated Intramolecular Epoxide-Opening Reaction

  摘要：

  We developed a new method for the stereocontrolled synthesis of cyclic oligoglycerols. Optically pure solketal and epichlorohydrin were coupled with allyl alcohol under aqueous basic conditions to construct a linear triglycerol skeleton. After subsequent steps, the epoxy alcohol (7) obtained was treated with a catalytic amount of BF3 center dot OEt2 in CH2Cl2 to produce in a high yield of the desired cyclic triglycerol through a regioselective, intramolecular epoxide ring-opening reaction.

  DOI：

  10.3987/com-12-s(n)67