ethyl 4-[N-(t-butyloxycarbonyl)amino]-2,3-dihydroxy-2-methyl-butanoate | 881206-24-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: ethyl 4-[N-(t-butyloxycarbonyl)amino]-2,3-dihydroxy-2-methyl-butanoate
• CAS: 881206-24-2
• 化学式: C₁₂H₂₃NO₆
• 分子量: 277.318
• InChiKey: YUHCNKRDYVBEPD-PRHODGIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  105.09
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-[N-(t-butyloxycarbonyl)amino]-2,3-dihydroxy-2-methyl-butanoate 在 盐酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 APTS 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4R,5R)-5-{[(E)-3-(3,4-Dimethoxy-phenyl)-acryloylamino]-methyl}-2,2,4-trimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester
  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：

  三乙基2-膦酰基丙酯 在 正丁基锂 、 甲基磺酰胺 、 AD-mix-β 作用下， 以 四氢呋喃 、 正己烷 、 水 、 叔丁醇 为溶剂， 反应 3.5h， 生成 ethyl 4-[N-(t-butyloxycarbonyl)amino]-2,3-dihydroxy-2-methyl-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