N-(Benzyloxycarbonyl)-O-(carboxymethyl)-L-serine α-tert-butyl ester | 144156-30-9

• 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: N-(Benzyloxycarbonyl)-O-(carboxymethyl)-L-serine α-tert-butyl ester
• 英文别名: 2-[(2S)-3-[(2-methylpropan-2-yl)oxy]-3-oxo-2-(phenylmethoxycarbonylamino)propoxy]acetic acid
• CAS: 144156-30-9
• 化学式: C₁₇H₂₃NO₇
• 分子量: 353.372
• InChiKey: YAEFQZBUOGYXHW-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  叔丁基三氯乙酰亚胺酯 、 N-(Benzyloxycarbonyl)-O-(carboxymethyl)-L-serine α-tert-butyl ester 以 二氯甲烷 、 环己烷 为溶剂， 反应 30.0h， 以89%的产率得到N-(Benzyloxycarbonyl)-O-(carboxymethyl)-L-serine di-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：

  N-苄氧羰基-L-丝氨酸 在 盐酸 、 4-二甲氨基吡啶 、 ruthenium trichloride 、 sodium periodate 、 二甲基硫 、 三氟化硼乙醚 、 sodium hexamethyldisilazane 、 臭氧 作用下， 以 1,4-二氧六环 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 104.75h， 生成 N-(Benzyloxycarbonyl)-O-(carboxymethyl)-L-serine α-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

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.