2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-2-[(E)-(3S,4S)-4-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-4-hydroxy-3-methyl-but-1-enyloxy]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester | 199526-21-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-2-[(E)-(3S,4S)-4-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-4-hydroxy-3-methyl-but-1-enyloxy]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3R,4S,5R,6S)-6-[(E,3S,4S)-4-[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]-4-hydroxy-3-methylbut-1-enoxy]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 199526-21-1
• 化学式: C₄₀H₆₄O₁₁
• 分子量: 720.942
• InChiKey: ZKQUSHOWMDZQHE-IXDOMSBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  51
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-2-[(E)-(3S,4S)-4-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-4-hydroxy-3-methyl-but-1-enyloxy]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Asymmetric allylation of aldehydes using tiglyltitanocenes attached to a carbohydrate

  摘要：

  eta(3)-Tiglyltitanium complexes bearing alpha- or beta-glucopyranosyl auxiliaries were synthesized starting from the corresponding C1-dienopyranosides. These complexes were reacted with propanal and (-)-myrtenal to afford 4-hydroxy-3-methylvinylglycoside derivatives. In several cases, high diastereofacial selectivities were obtained. Thus, the reaction employing (-)-myrtenal and beta-glucopyranosyl tiglyltitanium complex led to the unique (d.s.greater than or equal to 98%) 3R/4R-configurated compound bearing the sugar and pinenyl fragments, which can be considered as a promising new chiron. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10029-1
• 作为产物：
  描述：

  桃金娘烯醛 、 2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-2-[((E)-buta-1,3-dienyl)oxy]-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 在 二氯二茂钛 、 异丙基氯化镁 作用下， 生成 2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-2-[(E)-(3R,4R)-4-((1S,5R)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-4-hydroxy-3-methyl-but-1-enyloxy]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 、 2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-2-[(E)-(3R,4R)-4-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-4-hydroxy-3-methyl-but-1-enyloxy]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 、 2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-2-[(E)-(3S,4S)-4-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-4-hydroxy-3-methyl-but-1-enyloxy]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Asymmetric allylation of aldehydes using tiglyltitanocenes attached to a carbohydrate

  摘要：

  eta(3)-Tiglyltitanium complexes bearing alpha- or beta-glucopyranosyl auxiliaries were synthesized starting from the corresponding C1-dienopyranosides. These complexes were reacted with propanal and (-)-myrtenal to afford 4-hydroxy-3-methylvinylglycoside derivatives. In several cases, high diastereofacial selectivities were obtained. Thus, the reaction employing (-)-myrtenal and beta-glucopyranosyl tiglyltitanium complex led to the unique (d.s.greater than or equal to 98%) 3R/4R-configurated compound bearing the sugar and pinenyl fragments, which can be considered as a promising new chiron. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10029-1