methyl (5Z,2S)-2-di-tert-butoxycarbonylaminoeicos-5-enoate | 206128-04-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (5Z,2S)-2-di-tert-butoxycarbonylaminoeicos-5-enoate
• 英文别名: methyl (Z,2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]icos-5-enoate
• CAS: 206128-04-3
• 化学式: C₃₁H₅₇NO₆
• 分子量: 539.797
• InChiKey: WJEROEWYBOGSQH-BVBZGZSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  38
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (5Z,2S)-2-di-tert-butoxycarbonylaminoeicos-5-enoate 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.5h， 生成 (Z)-(S)-2-Amino-icos-5-enoic acid
  参考文献：
  名称：

  Enantiospecific synthesis of α-amino acid semialdehydes: a key step for the synthesis of unnatural unsaturated and saturated α-amino acids

  摘要：

  The enantiospecific synthesis of unnatural unsaturated and saturated alpha-amino acids based on a Wittig type reaction is described. The versatile synthetic intermediates, L-glutamic and L-aspartic acid semialdehydes, are obtained from the corresponding N,N-di-Boc-diesters, by the selective reduction of the omega'-ester with DIBAL(R) under controlled conditions. The semialdehydes are chemically stable for a prolonged time and react with various phosphorous ylides, under controlled conditions, to produce the enantiomerically pure unsaturated alpha-amino acids in high yields. The method is equally applicable to homologated diesters obtained by the presented methodology providing unsaturated amino acids with variable unsaturated positions and geometries. The corresponding saturated products can be obtained by simple hydrogenation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00354-1
• 作为产物：
  描述：

  谷氨酸二甲酯 在 4-二甲氨基吡啶 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 2.33h， 生成 methyl (5Z,2S)-2-di-tert-butoxycarbonylaminoeicos-5-enoate
  参考文献：
  名称：

  Enantiospecific synthesis of α-amino acid semialdehydes: a key step for the synthesis of unnatural unsaturated and saturated α-amino acids

  摘要：

  The enantiospecific synthesis of unnatural unsaturated and saturated alpha-amino acids based on a Wittig type reaction is described. The versatile synthetic intermediates, L-glutamic and L-aspartic acid semialdehydes, are obtained from the corresponding N,N-di-Boc-diesters, by the selective reduction of the omega'-ester with DIBAL(R) under controlled conditions. The semialdehydes are chemically stable for a prolonged time and react with various phosphorous ylides, under controlled conditions, to produce the enantiomerically pure unsaturated alpha-amino acids in high yields. The method is equally applicable to homologated diesters obtained by the presented methodology providing unsaturated amino acids with variable unsaturated positions and geometries. The corresponding saturated products can be obtained by simple hydrogenation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00354-1

文献信息

• A General Approach to the Asymmetric Synthesis of Unsaturated Lipidic α-Amino Acids. The First Synthesis of α-Aminoarachidonic Acid
  作者：George Kokotos、José M. Padrón、Tomás Martín、William A. Gibbons、Víctor S. Martín

  DOI：10.1021/jo9715128

  日期：1998.5.1