(Z)-3-Amino-4-phenyl-4-trimethylsilanyloxy-but-2-enoic acid tert-butyl ester | 206352-59-2

• 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: (Z)-3-Amino-4-phenyl-4-trimethylsilanyloxy-but-2-enoic acid tert-butyl ester
• 英文别名: tert-butyl (Z)-3-amino-4-phenyl-4-trimethylsilyloxybut-2-enoate
• CAS: 206352-59-2
• 化学式: C₁₇H₂₇NO₃Si
• 分子量: 321.492
• InChiKey: JOUAHJTUAZAFAX-OWBHPGMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-Amino-4-phenyl-4-trimethylsilanyloxy-but-2-enoic acid tert-butyl ester 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以88%的产率得到3-Amino-4-hydroxy-4-phenyl-butyric acid tert-butyl ester
  参考文献：
  名称：

  Application of the Blaise reaction: stereoselective synthesis of (4R)-tert-butyl 3-amino-4-trimethylsilyloxy-2-alkenoates from (R)-cyanohydrins

  摘要：

  O-Trimethylsilyl protected (R)-cyanohydrins 3 react with Reformatsky reagents from tert-butyl 2-bromoesters 4 and zinc dust (Blaise reaction) to give the corresponding addition products in high yields. Workup with an aqueous solution of NH4Cl at low temperature gives (4R)-tert-butyl 3-amino-4-trimethylsilyloxy-2-alkenoates (R)-5 without racemization. Hydrogenation of the alkenoates 5 to the corresponding tert-butyl beta-amino-gamma-hydroxyalkanoates 6, resulting in a mixture of two diastereoisomers, was only possible under special hydrogenation conditions. With HCl in dichloromethane compounds 6 cyclize to the corresponding beta-amino-gamma-hydroxybutyrolactones 8. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00039-1
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 α-(三甲基硅氧基)苯乙腈 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以74%的产率得到(Z)-3-Amino-4-phenyl-4-trimethylsilanyloxy-but-2-enoic acid tert-butyl ester
  参考文献：
  名称：

  Application of the Blaise reaction: stereoselective synthesis of (4R)-tert-butyl 3-amino-4-trimethylsilyloxy-2-alkenoates from (R)-cyanohydrins

  摘要：

  O-Trimethylsilyl protected (R)-cyanohydrins 3 react with Reformatsky reagents from tert-butyl 2-bromoesters 4 and zinc dust (Blaise reaction) to give the corresponding addition products in high yields. Workup with an aqueous solution of NH4Cl at low temperature gives (4R)-tert-butyl 3-amino-4-trimethylsilyloxy-2-alkenoates (R)-5 without racemization. Hydrogenation of the alkenoates 5 to the corresponding tert-butyl beta-amino-gamma-hydroxyalkanoates 6, resulting in a mixture of two diastereoisomers, was only possible under special hydrogenation conditions. With HCl in dichloromethane compounds 6 cyclize to the corresponding beta-amino-gamma-hydroxybutyrolactones 8. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00039-1

文献信息

• Application of the Blaise reaction: stereoselective synthesis of (4R)-tert-butyl 3-amino-4-trimethylsilyloxy-2-alkenoates from (R)-cyanohydrins
  作者：Jana Syed、Siegfried Förster、Franz Effenberger

  DOI：10.1016/s0957-4166(98)00039-1

  日期：1998.3

  O-Trimethylsilyl protected (R)-cyanohydrins 3 react with Reformatsky reagents from tert-butyl 2-bromoesters 4 and zinc dust (Blaise reaction) to give the corresponding addition products in high yields. Workup with an aqueous solution of NH4Cl at low temperature gives (4R)-tert-butyl 3-amino-4-trimethylsilyloxy-2-alkenoates (R)-5 without racemization. Hydrogenation of the alkenoates 5 to the corresponding tert-butyl beta-amino-gamma-hydroxyalkanoates 6, resulting in a mixture of two diastereoisomers, was only possible under special hydrogenation conditions. With HCl in dichloromethane compounds 6 cyclize to the corresponding beta-amino-gamma-hydroxybutyrolactones 8. (C) 1998 Elsevier Science Ltd. All rights reserved.