(((5S,6S)-6-(2-(benzyloxy)ethyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl)methoxy)(tert-butyl)dimethylsilane | 1190239-46-3

• 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: (((5S,6S)-6-(2-(benzyloxy)ethyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl)methoxy)(tert-butyl)dimethylsilane
• 英文别名: tert-butyl-dimethyl-[[(2S,3S)-3-methyl-2-(2-phenylmethoxyethyl)-3,4-dihydro-2H-pyran-6-yl]methoxy]silane
• CAS: 1190239-46-3
• 化学式: C₂₂H₃₆O₃Si
• 分子量: 376.612
• InChiKey: LHLFMKAPOMNMQI-RXVVDRJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (((5S,6S)-6-(2-(benzyloxy)ethyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl)methoxy)(tert-butyl)dimethylsilane 在 dimethyl sulfide borane 、 水 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(2R,3S,5S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methyl-6-(2-phenylmethoxyethyl)oxan-3-ol
  参考文献：
  名称：

  Total Synthesis of Brevisamide

  摘要：

  A convergent synthesis of brevisamide (1) is described based on the application of the crotyl silane-based [4 + 2]-annulation used for the preparation of the advanced oxygenated tetrahydropyran intermediate 2. The side chain bearing a conjugated (E,E)-diene was efficiently constructed under modified Negishi cross-coupling conditions.

  DOI：

  10.1021/ol901801h
• 作为产物：
  描述：

  ((2S,3S)-2-(2-(benzyloxy)ethyl)-3-methyl-3,4-dihydro-2H-pyran-6-yl)methanol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以590 mg的产率得到(((5S,6S)-6-(2-(benzyloxy)ethyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl)methoxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Total Synthesis of Brevisamide

  摘要：

  A convergent synthesis of brevisamide (1) is described based on the application of the crotyl silane-based [4 + 2]-annulation used for the preparation of the advanced oxygenated tetrahydropyran intermediate 2. The side chain bearing a conjugated (E,E)-diene was efficiently constructed under modified Negishi cross-coupling conditions.

  DOI：

  10.1021/ol901801h

文献信息

• Total Synthesis of Brevisamide
  作者：Jihoon Lee、James S. Panek

  DOI：10.1021/ol901801h

  日期：2009.10.1

  A convergent synthesis of brevisamide (1) is described based on the application of the crotyl silane-based [4 + 2]-annulation used for the preparation of the advanced oxygenated tetrahydropyran intermediate 2. The side chain bearing a conjugated (E,E)-diene was efficiently constructed under modified Negishi cross-coupling conditions.