N²-(tert-Butoxycarbonyl)-N³-(benzyloxycarbonyl)-N³-(carboxymethyl)-L-2,3-diaminopropanoic acid α-tert-butyl δ-allyl ester | 144156-18-3

• 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: N²-(tert-Butoxycarbonyl)-N³-(benzyloxycarbonyl)-N³-(carboxymethyl)-L-2,3-diaminopropanoic acid α-tert-butyl δ-allyl ester
• 英文别名: tert-butyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[(2-oxo-2-prop-2-enoxyethyl)-phenylmethoxycarbonylamino]propanoate
• CAS: 144156-18-3
• 化学式: C₂₅H₃₆N₂O₈
• 分子量: 492.569
• InChiKey: IHXWQQOECWTHFL-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N²-(tert-Butoxycarbonyl)-N³-(benzyloxycarbonyl)-N³-(carboxymethyl)-L-2,3-diaminopropanoic acid α-tert-butyl δ-allyl ester 在 吡啶 、 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 17.0h， 生成 (S)-3-(Allyloxycarbonylmethyl-benzyloxycarbonyl-amino)-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propionic acid tert-butyl ester
  参考文献：
  名称：

  Orthogonally protected N3-(carboxymethyl)-L-2,3-diaminopropanoic acids and O-(carboxymethyl)-L-serines for solid-phase peptide synthesis

  摘要：

  The syntheses of the orthogonally protected N3-(carboxymethyl)-2,3-L-diaminopropanoic acids 18, 19, and 20 and O-(carboxymethyl)-L-serines 35 and 38 are described. All of the diaminopropanoic acids were prepared via reductive amination of the known oxazolidine aldehyde 9. The carboxymethyl serines were prepared via 0-alkylation of N-CBZ-L-serine. To enable incorporation of these amino acids into cyclic peptides, protecting group schemes were designed for compatibility with either Boc or Fmoc solid-phase peptide synthesis.

  DOI：

  10.1021/jo00050a013
• 作为产物：
  描述：

  Boc-Gly-OAll 在 盐酸 、 jones reagent 、 sodium cyanoborohydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 环己烷 、 水 、 丙酮 为溶剂， 反应 65.0h， 生成 N²-(tert-Butoxycarbonyl)-N³-(benzyloxycarbonyl)-N³-(carboxymethyl)-L-2,3-diaminopropanoic acid α-tert-butyl δ-allyl ester
  参考文献：
  名称：

  Orthogonally protected N3-(carboxymethyl)-L-2,3-diaminopropanoic acids and O-(carboxymethyl)-L-serines for solid-phase peptide synthesis

  摘要：

  The syntheses of the orthogonally protected N3-(carboxymethyl)-2,3-L-diaminopropanoic acids 18, 19, and 20 and O-(carboxymethyl)-L-serines 35 and 38 are described. All of the diaminopropanoic acids were prepared via reductive amination of the known oxazolidine aldehyde 9. The carboxymethyl serines were prepared via 0-alkylation of N-CBZ-L-serine. To enable incorporation of these amino acids into cyclic peptides, protecting group schemes were designed for compatibility with either Boc or Fmoc solid-phase peptide synthesis.

  DOI：

  10.1021/jo00050a013

文献信息

• Orthogonally protected N3-(carboxymethyl)-L-2,3-diaminopropanoic acids and O-(carboxymethyl)-L-serines for solid-phase peptide synthesis
  作者：Mark S. Stanley

  DOI：10.1021/jo00050a013

  日期：1992.11

  The syntheses of the orthogonally protected N3-(carboxymethyl)-2,3-L-diaminopropanoic acids 18, 19, and 20 and O-(carboxymethyl)-L-serines 35 and 38 are described. All of the diaminopropanoic acids were prepared via reductive amination of the known oxazolidine aldehyde 9. The carboxymethyl serines were prepared via 0-alkylation of N-CBZ-L-serine. To enable incorporation of these amino acids into cyclic peptides, protecting group schemes were designed for compatibility with either Boc or Fmoc solid-phase peptide synthesis.