(S)-methyl 2-((S)-2-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)ethaneselenoamido)-3-phenylpropaneselenoamido)-4-methylpentanoate | 1361510-13-5

• 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: (S)-methyl 2-((S)-2-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)ethaneselenoamido)-3-phenylpropaneselenoamido)-4-methylpentanoate
• 英文别名: Fmoc-Gly-ψ-[CSe-NH]-Phe-ψ-[CSe-NH]-Leu-OMe
• CAS: 1361510-13-5
• 化学式: C₃₃H₃₇N₃O₄Se₂
• 分子量: 697.594
• InChiKey: HWESJCZIVRCHPN-VMPREFPWSA-N

反应信息

• 作为产物：
  描述：

  methyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycyl-L-phenylalanyl-L-leucinate 在 五氯化磷 、 N,N-二甲基甲酰胺 、 selenium 、 lithium aluminium tetrahydride 作用下， 以 苯 、 四氢呋喃 为溶剂， 反应 1.0h， 以76%的产率得到(S)-methyl 2-((S)-2-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)ethaneselenoamido)-3-phenylpropaneselenoamido)-4-methylpentanoate
  参考文献：
  名称：

  Synthesis of Selenoxo Peptides and Oligoselenoxo Peptides Employing LiAlHSeH

  摘要：

  Synthesis of selenoxo peptides by the treatment of N-a-protected peptide esters with a combination of PCl5 and LiAlHSeH is delineated. The method is simple, high-yielding, and free from racemization. Thus obtained selenoxo peptides are used as unit; for N-terminal chain extension through N-alpha-deprotection/coupling to yield peptide selenoxo peptide hybrids. Multiple selenation is demonstrated by conversion of two peptide bonds of tripeptides into selenoxo peptide bonds. Amino acid derived arylamides are also converted into aryl selenoamides. C6H5-CSeNH-Val-OMe 8f is obtained as single crystal, and its structure was determined through X-ray diffraction study.

  DOI：

  10.1021/jo2024703