tert-butyl-[[(4R,5R)-5-heptyl-2,2-dioxo-1,3,2-dioxathiolan-4-yl]methoxy]-dimethylsilane | 155930-99-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: tert-butyl-[[(4R,5R)-5-heptyl-2,2-dioxo-1,3,2-dioxathiolan-4-yl]methoxy]-dimethylsilane
• CAS: 155930-99-7
• 化学式: C₁₆H₃₄O₅SSi
• 分子量: 366.594
• InChiKey: GVXZVLAGTNHEEZ-HUUCEWRRSA-N

物化性质

• 沸点：
  403.5±14.0 °C(predicted)
• 密度：
  1.019±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl-[[(4R,5R)-5-heptyl-2,2-dioxo-1,3,2-dioxathiolan-4-yl]methoxy]-dimethylsilane 以86%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：

  反式-2-癸烯醇 在 4-二甲氨基吡啶 、 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 甲基磺酰胺 、 AD-mix-β 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 7.17h， 生成 tert-butyl-[[(4R,5R)-5-heptyl-2,2-dioxo-1,3,2-dioxathiolan-4-yl]methoxy]-dimethylsilane
  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

文献信息

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

  DOI：——

  日期：——
• An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction
  作者：Soo Y. Ko、Majbeen Malik、A. Frances Dickinson

  DOI：10.1021/jo00088a045

  日期：1994.5

  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.