(S)-2-((S)-2-Acryloylamino-3-phenyl-propionylamino)-3-hydroxy-propionic acid methyl ester | 521305-75-9

• 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)-2-((S)-2-Acryloylamino-3-phenyl-propionylamino)-3-hydroxy-propionic acid methyl ester
• CAS: 521305-75-9
• 化学式: C₁₆H₂₀N₂O₅
• 分子量: 320.345
• InChiKey: XEJPXWFHEMFEGM-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.45
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  104.73
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-((S)-2-Acryloylamino-3-phenyl-propionylamino)-3-hydroxy-propionic acid methyl ester 、 Cbz-phenylalanine 4-pyridylthioester 在 samarium diiodide 作用下， 以 乙腈 为溶剂， 以54%的产率得到2-[2-(5-benzyloxycarbonylamino-4-oxo-6-phenyl-hexanoylamino)-3-phenylpropionylamino]-3-hydroxy-propionic acid methyl ester
  参考文献：
  名称：

  SmI₂ Reduced Thioesters as Synthons of Unstable Acyl Radicals:  Direct Synthesis of Potential Protease Inhibitors via Intermolecular Radical Addition

  摘要：

  Aromatic alpha-heterosubstituted thioesters were found to undergo radical 1,4-addition reactions to a series of alpha,beta-unsaturated amides and one ester when subjected to the single electron reducing agent, samarium diiodide, at -78 degrees C. These thioesters derived from alpha-amino acids represent a synthetically useful synthon of unstable acyl radicals. This reaction conveniently provides access to gamma-ketoamides and esters in yields up to 90%, structures that are common in various protease inhibitors derived from peptides. Examples with acryloyl and methacryloyl derivatives of alpha-amino acids and dipeptides lead directly to tri- and tetrapeptide mimetics possessing the gamma-ketoamide functionality. No epimerization was observed with the mild conditions used for these reactions.

  DOI：

  10.1021/ja029662+
• 作为产物：
  描述：

  L-苯丙氨酰-L-丝氨酸 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-((S)-2-Acryloylamino-3-phenyl-propionylamino)-3-hydroxy-propionic acid methyl ester
  参考文献：
  名称：

  Cross‐metathesis ofC‐Glycosides and Peptides

  摘要：

  Peptides bearing an acryloyl residue at their N-terminus were coupled with various C-glycosides in an equimolar ratio via cross-metathesis. The newly formed olefin was obtained with high E/Z selectivity in satisfying to high yields with low homodimerization of the starting materials. The posttranslational cross-metathesis approach was shown to be suitable for the combinatorial synthesis of a small library of C-glycopeptides.

  DOI：

  10.1080/00397910701481146