tert-butyl (3R)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutanoate | 245323-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (3R)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutanoate
• 英文别名: tert-butyl (3R)-4-phenyl-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 245323-42-6
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: ZEVUWVOKKACHRQ-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutanoate 在 二甲基硫 作用下， 以 二氯甲烷 、 三氟乙酸 为溶剂， 反应 3.0h， 以95%的产率得到(3R)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutanoic acid
  参考文献：
  名称：

  A General Method for the Synthesis of Enantiomerically Pure β-Substituted, β-Amino Acids through α-Substituted Succinic Acid Derivatives

  摘要：

  A general procedure for the synthesis of enantiopure beta-substituted, beta-amino acids is presented. Alkylation of the sodium enolates derived from chiral N-acyloxazolidinone imides 2 (R = Me, i-Pr, t-Bu, Ph, Bn) with tert-butyl bromoacetate afforded the 2-substituted succinate derivatives 3 in good yields (82-89%) and with high selectivity (greater than or equal to 93:7). Following hydrolysis, Curtius rearrangement of the resulting carboxylic acid provided the enantiopure benzyloxycarbonyl (Cbz)-protected beta-amino esters 6 in good yields (74-79%).

  DOI：

  10.1021/jo990756k
• 作为产物：
  描述：

  (S)-4-苄基-3-(3-苯基丙酰基)噁唑烷丁-2-酮 在 lithium hydroxide 、 二苯基磷酸 、 双氧水 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 8.5h， 生成 tert-butyl (3R)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutanoate
  参考文献：
  名称：

  A General Method for the Synthesis of Enantiomerically Pure β-Substituted, β-Amino Acids through α-Substituted Succinic Acid Derivatives

  摘要：

  A general procedure for the synthesis of enantiopure beta-substituted, beta-amino acids is presented. Alkylation of the sodium enolates derived from chiral N-acyloxazolidinone imides 2 (R = Me, i-Pr, t-Bu, Ph, Bn) with tert-butyl bromoacetate afforded the 2-substituted succinate derivatives 3 in good yields (82-89%) and with high selectivity (greater than or equal to 93:7). Following hydrolysis, Curtius rearrangement of the resulting carboxylic acid provided the enantiopure benzyloxycarbonyl (Cbz)-protected beta-amino esters 6 in good yields (74-79%).

  DOI：

  10.1021/jo990756k

文献信息

• A General Method for the Synthesis of Enantiomerically Pure β-Substituted, β-Amino Acids through α-Substituted Succinic Acid Derivatives
  作者：David A. Evans、Leester D. Wu、John J. M. Wiener、Jeffrey S. Johnson、David H. B. Ripin、Jason S. Tedrow

  DOI：10.1021/jo990756k

  日期：1999.8.1

  A general procedure for the synthesis of enantiopure beta-substituted, beta-amino acids is presented. Alkylation of the sodium enolates derived from chiral N-acyloxazolidinone imides 2 (R = Me, i-Pr, t-Bu, Ph, Bn) with tert-butyl bromoacetate afforded the 2-substituted succinate derivatives 3 in good yields (82-89%) and with high selectivity (greater than or equal to 93:7). Following hydrolysis, Curtius rearrangement of the resulting carboxylic acid provided the enantiopure benzyloxycarbonyl (Cbz)-protected beta-amino esters 6 in good yields (74-79%).