triethyl-[(1S)-1-[(2R,3S)-3-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]oxiran-2-yl]-2-(triethylsilyloxymethyl)prop-2-enoxy]silane | 1226967-02-7

• 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: triethyl-[(1S)-1-[(2R,3S)-3-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]oxiran-2-yl]-2-(triethylsilyloxymethyl)prop-2-enoxy]silane
• CAS: 1226967-02-7
• 化学式: C₂₉H₅₂O₅Si₂
• 分子量: 536.9
• InChiKey: CRMFEPUTFVQIIA-FWDASRDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  36
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  triethyl-[(1S)-1-[(2R,3S)-3-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]oxiran-2-yl]-2-(triethylsilyloxymethyl)prop-2-enoxy]silane 在 四氧化锇 、 (DHQD)2PHAL 、 AD mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 96.0h， 生成 C₂₉H₅₄O₇Si₂ 、 C₂₉H₅₄O₇Si₂
  参考文献：
  名称：

  Enantioselective Synthesis of α-Methylene-β-hydroxy Carboxylic Acid Derivatives via a Diastereoselective Aldol/β-Elimination Sequence: Application to the C(15)−C(21) Fragment of Tedanolide C

  摘要：

  An enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and beta-elimination sequence utilizing the chiral beta-(phenylselenyl)propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.

  DOI：

  10.1021/ol1006955
• 作为产物：
  描述：

  三乙基氯硅烷 、 (S)-1-((2S,3S)-3-((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)oxiran-2-yl)-2-methylenepropane-1,3-diol 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以94%的产率得到triethyl-[(1S)-1-[(2R,3S)-3-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]oxiran-2-yl]-2-(triethylsilyloxymethyl)prop-2-enoxy]silane
  参考文献：
  名称：

  Enantioselective Synthesis of α-Methylene-β-hydroxy Carboxylic Acid Derivatives via a Diastereoselective Aldol/β-Elimination Sequence: Application to the C(15)−C(21) Fragment of Tedanolide C

  摘要：

  An enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and beta-elimination sequence utilizing the chiral beta-(phenylselenyl)propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.

  DOI：

  10.1021/ol1006955

文献信息

• Enantioselective Synthesis of α-Methylene-β-hydroxy Carboxylic Acid Derivatives via a Diastereoselective Aldol/β-Elimination Sequence: Application to the C(15)−C(21) Fragment of Tedanolide C
  作者：Roland Barth、William R. Roush

  DOI：10.1021/ol1006955

  日期：2010.5.21

  An enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and beta-elimination sequence utilizing the chiral beta-(phenylselenyl)propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.