(12R,13S,14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-triethylsiloxy-12,13-epoxyhexadeca-3,5,7,9-tetraenoic acid methyl ester | 1054654-78-2

• 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: (12R,13S,14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-triethylsiloxy-12,13-epoxyhexadeca-3,5,7,9-tetraenoic acid methyl ester
• 英文别名: methyl (2E,3E,5E,7E,9E)-11-[(2R,3S)-3-[(1S)-3-[tert-butyl(diphenyl)silyl]oxy-1-triethylsilyloxypropyl]-2-cyanooxiran-2-yl]-2-ethylidene-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoate
• CAS: 1054654-78-2
• 化学式: C₄₄H₅₉NO₆Si₂
• 分子量: 754.127
• InChiKey: UNDRIANEZRUNIB-KARUKXEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  53
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (12R,13S,14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-triethylsiloxy-12,13-epoxyhexadeca-3,5,7,9-tetraenoic acid methyl ester 在 ammonium hydroxide 、 四丁基氟化铵 、 silica gel 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 NG-391
  参考文献：
  名称：

  The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule

  摘要：

  The stereocontrolled total synthesis of (+)-NG-391, a neuronal cell-protecting molecule, is described along with the determination of its absolute stereochemistry. The following reactions in this synthesis are particularly noteworthy: (1) The stereoselective construction of the conjugated (E,E,E,E,E)-pentaene from an (E,E,E)-alcohol using an IBX oxidation followed by stereoselective Horner-Emmons reaction. (2) The (E)-selective Knoevenagel condensation of a beta-ketonitrile with a chiral 2-alkoxyaldehyde prepared from (S)-malic acid. (3) A diastereoselective epoxidation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01290-5
• 作为产物：
  描述：

  Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate 在 咪唑 、 正丁基锂 、 pyridine-SO3 complex 、 ditrityl peroxide 、 二异丁基氢化铝 、 二甲基亚砜 、 ethylenediamine Tetraacetic Acid 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 5.5h， 生成 (12R,13S,14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-triethylsiloxy-12,13-epoxyhexadeca-3,5,7,9-tetraenoic acid methyl ester
  参考文献：
  名称：

  The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule

  摘要：

  The stereocontrolled total synthesis of (+)-NG-391, a neuronal cell-protecting molecule, is described along with the determination of its absolute stereochemistry. The following reactions in this synthesis are particularly noteworthy: (1) The stereoselective construction of the conjugated (E,E,E,E,E)-pentaene from an (E,E,E)-alcohol using an IBX oxidation followed by stereoselective Horner-Emmons reaction. (2) The (E)-selective Knoevenagel condensation of a beta-ketonitrile with a chiral 2-alkoxyaldehyde prepared from (S)-malic acid. (3) A diastereoselective epoxidation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01290-5

文献信息

• The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule
  作者：Yujiro Hayashi、Junichiro Yamaguchi、Mitsuru Shoji

  DOI：10.1016/s0040-4020(02)01290-5

  日期：2002.12

  The stereocontrolled total synthesis of (+)-NG-391, a neuronal cell-protecting molecule, is described along with the determination of its absolute stereochemistry. The following reactions in this synthesis are particularly noteworthy: (1) The stereoselective construction of the conjugated (E,E,E,E,E)-pentaene from an (E,E,E)-alcohol using an IBX oxidation followed by stereoselective Horner-Emmons reaction. (2) The (E)-selective Knoevenagel condensation of a beta-ketonitrile with a chiral 2-alkoxyaldehyde prepared from (S)-malic acid. (3) A diastereoselective epoxidation. (C) 2002 Elsevier Science Ltd. All rights reserved.