(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl]ethanol | 948850-78-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl]ethanol
• CAS: 948850-78-0
• 化学式: C₂₇H₅₆O₄Si
• 分子量: 472.825
• InChiKey: KLBHRWFRYXHFDE-DSITVLBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.98
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl]ethanol 在 4-二甲氨基吡啶 、 sodium azide 、 三氯化铁 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 (2S,3S,4S)-4-azido-2-tetradecyl-tetrahydrofuran-3-ol
  参考文献：
  名称：

  Stereoselective Synthesis of Cytotoxic Anhydrophytosphingosine Pachastrissamine [Jaspine B]

  摘要：

  [GRAPHICS]A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.

  DOI：

  10.1021/jo0707838
• 作为产物：
  描述：

  (S)-methyl 2-hydroxy-2((4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)acetate 在 咪唑 、 sodium tetrahydroborate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl]ethanol
  参考文献：
  名称：

  Stereoselective Synthesis of Cytotoxic Anhydrophytosphingosine Pachastrissamine [Jaspine B]

  摘要：

  [GRAPHICS]A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.

  DOI：

  10.1021/jo0707838