methyl (3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylate | 1416358-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylate
• CAS: 1416358-99-0
• 化学式: C₂₆H₃₂N₂O₅
• 分子量: 452.55
• InChiKey: QOKFYZKTMUQQAM-BWAGFHJFSA-N

反应信息

• 作为反应物：
  描述：

  methyl (3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylate 在 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (3S,4R)-N-benzyl-4-(benzyl((3S,4R)-4-(methoxycarbonyl)-2-oxo-1-((S)-1-phenylethyl)pyrrolidin-3-yl)carbamoyl)-2-oxo-1-((S)-1-phenylethyl)pyrrolidin-3-aminium 2,2,2-trifluoroacetate
  参考文献：
  名称：

  β-Peptoids: synthesis of a novel dimer having a fully extended conformation

  摘要：

  Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-gamma-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-beta-amino acids 5a,b in good yield and high purity. Starting from compound 6a, the corresponding beta-peptoid dimer 8 was prepared, together with its derivatives 9 and 10, these latter displaying conformational restriction about the peptide bond, as evidenced by NMR data.

  DOI：

  10.1007/s00726-012-1275-1
• 作为产物：
  描述：

  (3S,4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-[(1S)-1-phenylethyl]-3-{[phenylmethylene]amino}pyrrolidin-2-one 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 氟化铵 、 sodium hypochlorite 、 sodium tetrahydroborate 、 三乙胺 、 sodium bromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.17h， 生成 methyl (3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylate
  参考文献：
  名称：

  β-Peptoids: synthesis of a novel dimer having a fully extended conformation

  摘要：

  Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-gamma-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-beta-amino acids 5a,b in good yield and high purity. Starting from compound 6a, the corresponding beta-peptoid dimer 8 was prepared, together with its derivatives 9 and 10, these latter displaying conformational restriction about the peptide bond, as evidenced by NMR data.

  DOI：

  10.1007/s00726-012-1275-1