t-butyl-4-[(benzyloxycarbonyl)amino]-2-methyl-2-butanoate | 881206-06-0

• 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: t-butyl-4-[(benzyloxycarbonyl)amino]-2-methyl-2-butanoate
• 英文别名: tert-butyl (Z)-2-methyl-4-(phenylmethoxycarbonylamino)but-2-enoate
• CAS: 881206-06-0
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: OLCAFQADXDHYFL-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  t-butyl-4-[(benzyloxycarbonyl)amino]-2-methyl-2-butanoate 在 palladium on activated charcoal 甲基磺酰胺 、 AD-mix-β 、 氢气 作用下， 以 甲醇 、 水 、 叔丁醇 为溶剂， 20.0 ℃ 、3.0 MPa 条件下， 反应 60.0h， 生成 (2R,3R)-tert-butyl 4-amino-2,3-dihydroxy-2-methylbutanoate
  参考文献：
  名称：

  First stereoselective synthesis of potassium aeschynomate and its no-natural stereomers

  摘要：

  The synthesis of potassium aeshynomate and its non-natural stereomers was achieved using the Sharpless catalytic asymmetric dihydroxylation of (Z) or (E) vinylogous glycine as the key step. The resulting gamma-amino alpha, beta-dihydroxyester stereomer was deprotected and coupled with the caffeic acid to afford stereoselectively potassium aeshynomate or its stereomers. A detailed study of the NMR data of the different stereomers is reported that corrects the literature data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.051
• 作为产物：
  描述：

  N-alpha-Cbz-甘氨酸 N-甲氧基-N-甲酰胺 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 2.58h， 生成 t-butyl-4-[(benzyloxycarbonyl)amino]-2-methyl-2-butanoate
  参考文献：
  名称：

  First stereoselective synthesis of potassium aeschynomate and its no-natural stereomers

  摘要：

  The synthesis of potassium aeshynomate and its non-natural stereomers was achieved using the Sharpless catalytic asymmetric dihydroxylation of (Z) or (E) vinylogous glycine as the key step. The resulting gamma-amino alpha, beta-dihydroxyester stereomer was deprotected and coupled with the caffeic acid to afford stereoselectively potassium aeshynomate or its stereomers. A detailed study of the NMR data of the different stereomers is reported that corrects the literature data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.051