Nα-(4-nitrophenyloxycarbonyl)-L-isoleucine tert-butyl ester | 1042724-65-1

• 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: Nα-(4-nitrophenyloxycarbonyl)-L-isoleucine tert-butyl ester
• 英文别名: tert-butyl (2S,3S)-3-methyl-2-[(4-nitrophenoxy)carbonylamino]pentanoate
• CAS: 1042724-65-1
• 化学式: C₁₇H₂₄N₂O₆
• 分子量: 352.387
• InChiKey: JHBUOAXUDNFBLF-FZMZJTMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Nα-(4-nitrophenyloxycarbonyl)-L-isoleucine tert-butyl ester 在 N,N-二异丙基乙胺 作用下， 生成 tert-butyl (2S,3S)-2-isocyanato-3-methylpentanoate
  参考文献：
  名称：

  Solid-Support Based Total Synthesis and Stereochemical Correction of Brunsvicamide A

  摘要：

  A total synthesis of the cyanobacterial metabolite brunsvicamide A and the correction of its originally assigned stereochemistry are reported. Key elements were the construction of a urea building block, peptide elongation on solid phase, and on-resin cyclization of the peptide chain, with good overall yield. Detailed structural investigations uncovered that brunsvicamide A features a previously undetected D-lysine residue in its backbone, setting the foundation for all further investigations in this compound class.

  DOI：

  10.1021/ol801064d
• 作为产物：
  描述：

  L-异亮氨酸叔-丁基酯 、 对硝基苯基氯甲酸酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以87%的产率得到Nα-(4-nitrophenyloxycarbonyl)-L-isoleucine tert-butyl ester
  参考文献：
  名称：

  Solid-Support Based Total Synthesis and Stereochemical Correction of Brunsvicamide A

  摘要：

  A total synthesis of the cyanobacterial metabolite brunsvicamide A and the correction of its originally assigned stereochemistry are reported. Key elements were the construction of a urea building block, peptide elongation on solid phase, and on-resin cyclization of the peptide chain, with good overall yield. Detailed structural investigations uncovered that brunsvicamide A features a previously undetected D-lysine residue in its backbone, setting the foundation for all further investigations in this compound class.

  DOI：

  10.1021/ol801064d

文献信息

• Solid-Support Based Total Synthesis and Stereochemical Correction of Brunsvicamide A
  作者：Thilo Walther、Hans-Dieter Arndt、Herbert Waldmann

  DOI：10.1021/ol801064d

  日期：2008.8.7

  A total synthesis of the cyanobacterial metabolite brunsvicamide A and the correction of its originally assigned stereochemistry are reported. Key elements were the construction of a urea building block, peptide elongation on solid phase, and on-resin cyclization of the peptide chain, with good overall yield. Detailed structural investigations uncovered that brunsvicamide A features a previously undetected D-lysine residue in its backbone, setting the foundation for all further investigations in this compound class.