tert-butyl (2S,3R)-2-<(9-phenylfluorenyl)amino>-3-methyl-4-hydroxybutanoate | 120230-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: tert-butyl (2S,3R)-2-<(9-phenylfluorenyl)amino>-3-methyl-4-hydroxybutanoate
• 英文别名: (2S,3R)-2-[(9-phenylfluoren-9-yl)amino]-3-methyl-4-hydroxybutanoic acid tert-butyl ester；t-butyl (2S,3R)-2-[(9-phenylfluoren-9-yl)amino]-3-methyl-4-hydroxybutanoate；tert-butyl (2S,3R)-4-hydroxy-3-methyl-2-[(9-phenylfluoren-9-yl)amino]butanoate
• CAS: 120230-47-9
• 化学式: C₂₈H₃₁NO₃
• 分子量: 429.559
• InChiKey: BZHQXTKKPPACSM-DFBJGRDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3R)-2-<(9-phenylfluorenyl)amino>-3-methyl-4-hydroxybutanoate 在 palladium on activated charcoal 吡啶 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 19.0h， 生成 tert-butyl (2S,3R)-2-<(benzoxycarbonyl)amino>-3-methyl-4-hydroxybutanoate
  参考文献：
  名称：

  Conformationally constrained peptides. Chirospecific synthesis of 4-alkyl-substituted .gamma.-lactam-bridged dipeptides from L-aspartic acid

  摘要：

  DOI：

  10.1021/jo00274a037
• 作为产物：
  描述：

  9-溴-9-苯基芴 在 三甲基氯硅烷 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 128.0h， 生成 tert-butyl (2S,3R)-2-<(9-phenylfluorenyl)amino>-3-methyl-4-hydroxybutanoate
  参考文献：
  名称：

  Synthesis of Optically Active 2-Alkyl-3,4-iminobutanoic Acids. β-Amino Acids Containing an Aziridine Heterocycle

  摘要：

  All four stereoisomers of 2-alkyl-3,4-iminobutanoic acid, a novel class of beta -amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the beta -position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the alpha -carboxylate and alpha -amino groups. The alpha -carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.

  DOI：

  10.1021/jo0014055

文献信息

• Native Chemical Ligation at Valine: A Contribution to Peptide and Glycopeptide Synthesis
  作者：Jin Chen、Qian Wan、Yu Yuan、Jianglong Zhu、Samuel J. Danishefsky

  DOI：10.1002/anie.200803523

  日期：2008.10.20
• WOLF, JEAN-PIERRE;RAPOPORT, HENRY, J. ORG. CHEM., 54,(1989) N3, C. 3164-3173
  作者：WOLF, JEAN-PIERRE、RAPOPORT, HENRY

  DOI：——

  日期：——
• Conformationally constrained peptides. Chirospecific synthesis of 4-alkyl-substituted .gamma.-lactam-bridged dipeptides from L-aspartic acid
  作者：Jean Pierre Wolf、Henry Rapoport

  DOI：10.1021/jo00274a037

  日期：1989.6
• Synthesis of Optically Active 2-Alkyl-3,4-iminobutanoic Acids. β-Amino Acids Containing an Aziridine Heterocycle
  作者：Jeong-il Park、Guan Rong Tian、Dong H. Kim

  DOI：10.1021/jo0014055

  日期：2001.6.1

  All four stereoisomers of 2-alkyl-3,4-iminobutanoic acid, a novel class of beta -amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the beta -position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the alpha -carboxylate and alpha -amino groups. The alpha -carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.