(2R,3S,5S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methyl-6-(2-phenylmethoxyethyl)oxan-3-ol | 1190239-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,5S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methyl-6-(2-phenylmethoxyethyl)oxan-3-ol
• CAS: 1190239-35-0
• 化学式: C₂₂H₃₈O₄Si
• 分子量: 394.627
• InChiKey: XXFMESLBAINMJA-ZIBCJSCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  (2R,3S,5S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methyl-6-(2-phenylmethoxyethyl)oxan-3-ol 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到((2R,3S,5S,6S)-6-(2-(benzyloxy)ethyl)-2-((tert-butyldimethylsilyloxy)methyl)-5-methyl-tetrahydro-2H-pyran-3-yloxy)(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
• 作为产物：
  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

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.