tert-butyl-benzyl ((3S,4R)-4-(hydroxymethyl)-1-((S)-1-(4-methoxyphenyl)ethyl)-2-oxopyrrolidin-3-yl)carbamate | 1416358-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: tert-butyl-benzyl ((3S,4R)-4-(hydroxymethyl)-1-((S)-1-(4-methoxyphenyl)ethyl)-2-oxopyrrolidin-3-yl)carbamate
• CAS: 1416358-96-7
• 化学式: C₂₆H₃₄N₂O₅
• 分子量: 454.566
• InChiKey: QAUOZBJHHOPXIF-HARLFGEKSA-N

反应信息

• 作为反应物：
  描述：

  tert-butyl-benzyl ((3S,4R)-4-(hydroxymethyl)-1-((S)-1-(4-methoxyphenyl)ethyl)-2-oxopyrrolidin-3-yl)carbamate 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium bromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 methyl (3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-1-((S)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidine-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
• 作为产物：
  描述：

  tert-butyl-benzyl ((3S,4R)-4-(((tert-butyldimethylsilyl)oxy)methyl)-1-((S)-1-(4-methoxyphenyl)ethyl)-2-oxopyrrolidin-3-yl)carbamate 在 氟化铵 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以90%的产率得到tert-butyl-benzyl ((3S,4R)-4-(hydroxymethyl)-1-((S)-1-(4-methoxyphenyl)ethyl)-2-oxopyrrolidin-3-yl)carbamate
  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