N²-(tert-Butoxycarbonyl)-N³-((9-fluorenylmethoxy)carbonyl)-N³-(carboxymethyl)-(2S)-diaminopropan-1-ol allyl ester | 144156-10-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N²-(tert-Butoxycarbonyl)-N³-((9-fluorenylmethoxy)carbonyl)-N³-(carboxymethyl)-(2S)-diaminopropan-1-ol allyl ester
• 英文别名: N²-(tert-Butoxycarbonyl)-N³-[(9-fluorenylmethoxy)carbonyl]-N³-(carboxymethyl)-(2S)-diaminopropan-1-ol allyl ester；prop-2-enyl 2-[9H-fluoren-9-ylmethoxycarbonyl-[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]acetate
• CAS: 144156-10-5
• 化学式: C₂₈H₃₄N₂O₇
• 分子量: 510.587
• InChiKey: IAVBZTGBRCNXGG-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N²-(tert-Butoxycarbonyl)-N³-((9-fluorenylmethoxy)carbonyl)-N³-(carboxymethyl)-(2S)-diaminopropan-1-ol allyl ester 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以83%的产率得到N²-(tert-Butoxycarbonyl)-N³-((9-fluorenylmethoxy)carbonyl)-N³-(carboxymethyl)-L-2,3-diaminopropanoic acid 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
• 作为产物：
  描述：

  Boc-Gly-OAll 在 盐酸 、 sodium cyanoborohydride 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 36.25h， 生成 N²-(tert-Butoxycarbonyl)-N³-((9-fluorenylmethoxy)carbonyl)-N³-(carboxymethyl)-(2S)-diaminopropan-1-ol 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