methyl 2-[[(2S)-4-methylsulfanyl-2-[[2-(prop-2-enoylamino)acetyl]amino]butanoyl]amino]acetate | 952312-63-9

• 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: methyl 2-[[(2S)-4-methylsulfanyl-2-[[2-(prop-2-enoylamino)acetyl]amino]butanoyl]amino]acetate
• CAS: 952312-63-9
• 化学式: C₁₃H₂₁N₃O₅S
• 分子量: 331.393
• InChiKey: VTBTZWUATHGIDO-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[[(2S)-4-methylsulfanyl-2-[[2-(prop-2-enoylamino)acetyl]amino]butanoyl]amino]acetate 、 3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene 在 substituted Grubbs-type ruthenium carbene complex 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以58%的产率得到methyl 2-[[(2S)-4-methylsulfanyl-2-[[2-[[(E)-4-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]but-2-enoyl]amino]acetyl]amino]butanoyl]amino]acetate
  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
• 作为产物：
  描述：

  甘氨酰-蛋氨酰-甘氨酸 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-[[(2S)-4-methylsulfanyl-2-[[2-(prop-2-enoylamino)acetyl]amino]butanoyl]amino]acetate
  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

文献信息

• Cross‐metathesis of<i>C</i>‐Glycosides and Peptides
  作者：Peter Brüchner、David Koch、Ulrike Voigtmann、Siegfried Blechert

  DOI：10.1080/00397910701481146

  日期：2007.8

  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.