(14S,17S,18S)-14,17,18-tris(triethylsilyloxy)octacosanoic acid | 1127644-98-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (14S,17S,18S)-14,17,18-tris(triethylsilyloxy)octacosanoic acid
• CAS: 1127644-98-7
• 化学式: C₄₆H₉₈O₅Si₃
• 分子量: 815.538
• InChiKey: PBFFKHMKFCSQJK-OFEBPFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.23
• 重原子数：
  54
• 可旋转键数：
  41
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,11bR)-3-amino-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one 、 (14S,17S,18S)-14,17,18-tris(triethylsilyloxy)octacosanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以54%的产率得到
  参考文献：
  名称：

  Enantioselective Synthesis of Schulzeines B and C via a β-Lactone-Derived Surrogate for Bishomoserine Aldehyde

  摘要：

  Enantioselective syntheses of the glucosidase inhibitors schulzeines B and C were achieved by employing a Pictet-Spengler reaction of a beta-lactone-derived masked bishomoserine aldehyde. Subsequent Corey-Link reaction unveiled an alpha-azido acid enabling cyclization to the delta-lactam fused tetrahydroisoquinoline. An efficient synthesis of the trisulfate-bearing side chain featured a Noyori hydrogenation and a Sharpless dihydroxylation. An unexpected reaction of a pendant amine during a Corey-Link process opens avenues for the synthesis of proline and related amino acid derivatives.

  DOI：

  10.1021/ol802992m
• 作为产物：
  描述：

  在 2,6-二甲基吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以95%的产率得到(14S,17S,18S)-14,17,18-tris(triethylsilyloxy)octacosanoic acid
  参考文献：
  名称：

  Enantioselective Synthesis of Schulzeines B and C via a β-Lactone-Derived Surrogate for Bishomoserine Aldehyde

  摘要：

  Enantioselective syntheses of the glucosidase inhibitors schulzeines B and C were achieved by employing a Pictet-Spengler reaction of a beta-lactone-derived masked bishomoserine aldehyde. Subsequent Corey-Link reaction unveiled an alpha-azido acid enabling cyclization to the delta-lactam fused tetrahydroisoquinoline. An efficient synthesis of the trisulfate-bearing side chain featured a Noyori hydrogenation and a Sharpless dihydroxylation. An unexpected reaction of a pendant amine during a Corey-Link process opens avenues for the synthesis of proline and related amino acid derivatives.

  DOI：

  10.1021/ol802992m