(2S,3S,4S)-1-[tert-butyl(dimethyl)silyl]oxy-2-methyl-4-[(4S,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl]pentan-3-ol | 1233512-06-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S)-1-[tert-butyl(dimethyl)silyl]oxy-2-methyl-4-[(4S,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl]pentan-3-ol
• CAS: 1233512-06-5
• 化学式: C₁₉H₄₀O₄Si
• 分子量: 360.61
• InChiKey: XLAAQAVPELNNCB-WOYTXXSLSA-N

物化性质

• 沸点：
  398.6±27.0 °C(predicted)
• 密度：
  0.929±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 (2S,3S,4S)-1-[tert-butyl(dimethyl)silyl]oxy-2-methyl-4-[(4S,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl]pentan-3-ol 、 碘甲烷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Application of desymmetrization protocol for the formal total synthesis of emericellamide B

  摘要：

  A highly convergent formal total synthesis of emericellamide B, a 19-membered antibacterial depsipeptide is described. The key feature of the strategy is the generation of four stereogenic centers from a bicyclic precursor via desymmetrization technique and utilization for emericellamide B and related natural product synthesis. (C) 2010 Elsevier Ltd. All tights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.015
• 作为产物：
  描述：

  (((2S,3S,4S)-3-(benzyloxy)-2-methyl-4-((4S,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl)pentyl)oxy)(tert-butyl)dimethylsilane 在 palladium 10% on activated carbon 、 氢气 作用下， 以 正己烷 为溶剂， 反应 12.0h， 以92%的产率得到(2S,3S,4S)-1-[tert-butyl(dimethyl)silyl]oxy-2-methyl-4-[(4S,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl]pentan-3-ol
  参考文献：
  名称：

  Application of desymmetrization protocol for the formal total synthesis of emericellamide B

  摘要：

  A highly convergent formal total synthesis of emericellamide B, a 19-membered antibacterial depsipeptide is described. The key feature of the strategy is the generation of four stereogenic centers from a bicyclic precursor via desymmetrization technique and utilization for emericellamide B and related natural product synthesis. (C) 2010 Elsevier Ltd. All tights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.015

文献信息

• Application of desymmetrization protocol for the formal total synthesis of emericellamide B
  作者：Debendra K. Mohapatra、Sk. Samad Hossain、Santu Dhara、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.04.015

  日期：2010.6

  A highly convergent formal total synthesis of emericellamide B, a 19-membered antibacterial depsipeptide is described. The key feature of the strategy is the generation of four stereogenic centers from a bicyclic precursor via desymmetrization technique and utilization for emericellamide B and related natural product synthesis. (C) 2010 Elsevier Ltd. All tights reserved.