N-(tert-Butoxycarbonyl)-O-(carboxymethyl)-L-serine α-tert-butyl δ-allyl ester | 144156-27-4

• 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-(tert-Butoxycarbonyl)-O-(carboxymethyl)-L-serine 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-enoxyethoxy)propanoate
• CAS: 144156-27-4
• 化学式: C₁₇H₂₉NO₇
• 分子量: 359.42
• InChiKey: GUYTUYIIMDNNLW-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(tert-Butoxycarbonyl)-O-(carboxymethyl)-L-serine α-tert-butyl δ-allyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 (S)-3-Allyloxycarbonylmethoxy-2-amino-propionic acid tert-butyl ester; hydrochloride
  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：

  O-allyl-N-carboxybenzyl-L-serine 在 palladium on activated charcoal 4-二甲氨基吡啶 、 ruthenium trichloride 、 sodium periodate 、 二甲基硫 、 三氟化硼乙醚 、 氢气 、 碳酸氢钠 、 臭氧 作用下， 以 甲醇 、 四氯化碳 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~50.0 ℃ 、344.73 kPa 条件下， 反应 104.0h， 生成 N-(tert-Butoxycarbonyl)-O-(carboxymethyl)-L-serine 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.