tert-Butyl-[(E)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyloxy]-dimethyl-silane | 155930-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-[(E)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyloxy]-dimethyl-silane
• 英文别名: tert-butyl-[(E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoxy]-dimethylsilane
• CAS: 155930-91-9
• 化学式: C₁₄H₂₈O₃Si
• 分子量: 272.46
• InChiKey: MKCADEMZZMNTDM-BCPZQOPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl-[(E)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyloxy]-dimethyl-silane 以96%的产率得到
  参考文献：
  名称：

  Ko Soo Y., Malik Majbeen, Dickinson A. Frances, J. Org. Chem, 59 (1994) N 9, S 2570-2576

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-4,5-异亚丙基-2-戊醇 、 叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 tert-Butyl-[(E)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyloxy]-dimethyl-silane
  参考文献：
  名称：

  An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction

  摘要：

  A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction. Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate. Upon desilylation, this compound undergoes a Payne-type rearrangement. Nucleophilic epoxide-opening then provides an erythro-2,3-diol. The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel. Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures. Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, N--(3), (OAc)-O--, (CN)-C--, halides as well as carbon nucleophiles and hydride.

  DOI：

  10.1021/jo00088a045