(2S,4S,6R)-2-[2-(4-hydroxyphenyl)ethyl]-6-tridecyltetrahydropyran-2,4-diol | 945736-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2S,4S,6R)-2-[2-(4-hydroxyphenyl)ethyl]-6-tridecyltetrahydropyran-2,4-diol
• 英文别名: (2S,4S,6R)-2-[2-(4-hydroxyphenyl)ethyl]-6-tridecyloxane-2,4-diol
• CAS: 945736-80-1
• 化学式: C₂₆H₄₄O₄
• 分子量: 420.633
• InChiKey: SBXKOLKGDDANAN-NXCFDTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4S,6R)-2-[2-(4-hydroxyphenyl)ethyl]-6-tridecyltetrahydropyran-2,4-diol 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 水 、 丙酮 为溶剂， 反应 5.25h， 生成 (+)-6-epi-aculeatin D
  参考文献：
  名称：

  Diastereodivergent Strategies for the Synthesis of Homochiral Aculeatins

  摘要：

  We report concise and stereocontrolled syntheses of aculeatins (-)-A, (+)-B, (+)-D, and (+)-6-epi-D. Diastereodivergent 1,3-inductions in Mukaiyama aldol coupling contribute to reduce steps and to increase flexibility with reactants having sterically restricted proximal substituents (i.e., CH2), involving either a good anti or a moderate syn 1,3-induction, depending on the nature of protecting group (P). In addition, the 3,5-syn-diol-ketone resulting from concomitant deprotection of the beta-alkoxy (Tr = trityl) group proves to be remarkably stable whereas the 3,5-anti diastereoisomer cyclizes spontaneously to the corresponding tetrahydropyran hemiketal, thus enabling a useful and facile separation. The second part of our study is devoted to improving the yield and the diastereoselectivity of the final phenolic oxidation reaction leading to aculeatins.

  DOI：

  10.1021/jo0707986
• 作为产物：
  描述：

  [(R)-((E)-1-but-2-enyl)tetradecyloxy]triisopropylsilane 在 四氧化锇 、 四丁基氟化铵 、 N-甲基吗啉氧化物 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 5.08h， 生成 (2S,4S,6R)-2-[2-(4-hydroxyphenyl)ethyl]-6-tridecyltetrahydropyran-2,4-diol
  参考文献：
  名称：

  Diastereodivergent Strategies for the Synthesis of Homochiral Aculeatins

  摘要：

  We report concise and stereocontrolled syntheses of aculeatins (-)-A, (+)-B, (+)-D, and (+)-6-epi-D. Diastereodivergent 1,3-inductions in Mukaiyama aldol coupling contribute to reduce steps and to increase flexibility with reactants having sterically restricted proximal substituents (i.e., CH2), involving either a good anti or a moderate syn 1,3-induction, depending on the nature of protecting group (P). In addition, the 3,5-syn-diol-ketone resulting from concomitant deprotection of the beta-alkoxy (Tr = trityl) group proves to be remarkably stable whereas the 3,5-anti diastereoisomer cyclizes spontaneously to the corresponding tetrahydropyran hemiketal, thus enabling a useful and facile separation. The second part of our study is devoted to improving the yield and the diastereoselectivity of the final phenolic oxidation reaction leading to aculeatins.

  DOI：

  10.1021/jo0707986

文献信息

• Diastereodivergent Strategies for the Synthesis of Homochiral Aculeatins
  作者：Marine Peuchmaur、Yung-Sing Wong

  DOI：10.1021/jo0707986

  日期：2007.7.1

  We report concise and stereocontrolled syntheses of aculeatins (-)-A, (+)-B, (+)-D, and (+)-6-epi-D. Diastereodivergent 1,3-inductions in Mukaiyama aldol coupling contribute to reduce steps and to increase flexibility with reactants having sterically restricted proximal substituents (i.e., CH2), involving either a good anti or a moderate syn 1,3-induction, depending on the nature of protecting group (P). In addition, the 3,5-syn-diol-ketone resulting from concomitant deprotection of the beta-alkoxy (Tr = trityl) group proves to be remarkably stable whereas the 3,5-anti diastereoisomer cyclizes spontaneously to the corresponding tetrahydropyran hemiketal, thus enabling a useful and facile separation. The second part of our study is devoted to improving the yield and the diastereoselectivity of the final phenolic oxidation reaction leading to aculeatins.