N-acryloyl-glycinyl-proline methyl ester | 952312-36-6

• 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: N-acryloyl-glycinyl-proline methyl ester
• 英文别名: methyl (2S)-1-[2-(prop-2-enoylamino)acetyl]pyrrolidine-2-carboxylate
• CAS: 952312-36-6
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: CKDYHERVIVPBRV-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acryloyl-glycinyl-proline methyl ester 、 3,4,5-tri-O-acetyl-2,6-anhydro-1,7,8,9-tetradeoxy-L-glycero-D-galacto-non-8-enitol 在 substituted Grubbs-type ruthenium carbene complex 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以36%的产率得到methyl (2S)-1-[2-[[(E)-4-[(2S,3R,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]but-2-enoyl]amino]acetyl]pyrrolidine-2-carboxylate
  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：

  甘油-L-脯氨酸 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-acryloyl-glycinyl-proline 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

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.