Carbonic acid (3R,5S)-1-acetyl-5-phenethylcarbamoyl-pyrrolidin-3-yl ester 2-oxo-2-(3,4,5-trimethoxy-phenyl)-ethyl ester | 828921-17-1

• 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: Carbonic acid (3R,5S)-1-acetyl-5-phenethylcarbamoyl-pyrrolidin-3-yl ester 2-oxo-2-(3,4,5-trimethoxy-phenyl)-ethyl ester
• CAS: 828921-17-1
• 化学式: C₂₇H₃₂N₂O₉
• 分子量: 528.559
• InChiKey: FOQGXKFVBHZULB-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  129.7
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Carbonic acid (3R,5S)-1-acetyl-5-phenethylcarbamoyl-pyrrolidin-3-yl ester 2-oxo-2-(3,4,5-trimethoxy-phenyl)-ethyl ester 在 1,4-环己二烯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以92%的产率得到(2S,4R)-1-Acetyl-4-hydroxy-pyrrolidine-2-carboxylic acid phenethyl-amide
  参考文献：
  名称：

  Light-Directed Radial Combinatorial Chemistry:  Orthogonal Safety-Catch Protecting Groups for the Synthesis of Small Molecule Microarrays

  摘要：

  We describe the development of photolabile protecting groups based on the 3,4,5-trimethoxyphenacyl group (TMP). Orthogonal safety-catches were created by introducing an acid-activatible dimethyl ketal (AA-TMP) and an oxidatively activatible 1,3-dithiane (OA-TMP) into the photolabile TMP group. We demonstrate the application of these protecting groups in light-directed synthesis of small molecule microarrays with diversity elements radially attached to a hydroxyproline scaffold.

  DOI：

  10.1021/ja044702q
• 作为产物：
  描述：

  [[(3R,5S)-5-(2-phenylethylcarbamoyl)pyrrolidin-3-yl]-[2-(3,4,5-trimethoxyphenyl)-1,3-dithian-2-yl]methyl] carbonate 在 TEA 、 过碘酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 Carbonic acid (3R,5S)-1-acetyl-5-phenethylcarbamoyl-pyrrolidin-3-yl ester 2-oxo-2-(3,4,5-trimethoxy-phenyl)-ethyl ester
  参考文献：
  名称：

  Light-Directed Radial Combinatorial Chemistry:  Orthogonal Safety-Catch Protecting Groups for the Synthesis of Small Molecule Microarrays

  摘要：

  We describe the development of photolabile protecting groups based on the 3,4,5-trimethoxyphenacyl group (TMP). Orthogonal safety-catches were created by introducing an acid-activatible dimethyl ketal (AA-TMP) and an oxidatively activatible 1,3-dithiane (OA-TMP) into the photolabile TMP group. We demonstrate the application of these protecting groups in light-directed synthesis of small molecule microarrays with diversity elements radially attached to a hydroxyproline scaffold.

  DOI：

  10.1021/ja044702q