(S)-2-[((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid allyl ester | 144156-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-2-[((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid allyl ester
• 英文别名: prop-2-enyl (2S)-6-[(2-chlorophenyl)methoxycarbonylamino]-2-[9H-fluoren-9-ylmethoxycarbonyl-[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]hexanoate
• CAS: 144156-12-7
• 化学式: C₄₀H₄₈ClN₃O₉
• 分子量: 750.289
• InChiKey: DZBMHBGFCHGEBO-WJVKJDHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  53.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  152.73
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid allyl ester 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以75%的产率得到(S)-2-[((S)-2-tert-Butoxycarbonylamino-2-carboxy-ethyl)-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid 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：

  (S)-4-{[[(S)-1-Allyloxycarbonyl-5-(2-chloro-benzyloxycarbonylamino)-pentyl]-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 盐酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 (S)-2-[((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid 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