(2S,4R)-2-Phenethylcarbamoyl-4-[2-(3,4,5-trimethoxy-phenyl)-[1,3]dithian-2-ylmethoxycarbonyloxy]-pyrrolidine-1-carboxylic acid 2,2-dimethoxy-2-(3,4,5-trimethoxy-phenyl)-ethyl ester | 828921-13-7

• 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: (2S,4R)-2-Phenethylcarbamoyl-4-[2-(3,4,5-trimethoxy-phenyl)-[1,3]dithian-2-ylmethoxycarbonyloxy]-pyrrolidine-1-carboxylic acid 2,2-dimethoxy-2-(3,4,5-trimethoxy-phenyl)-ethyl ester
• CAS: 828921-13-7
• 化学式: C₄₂H₅₄N₂O₁₄S₂
• 分子量: 875.028
• InChiKey: MLBNBPKXRIFJBP-JSOSNVBQSA-N

物化性质

• 沸点：
  959.3±65.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  60.0
• 可旋转键数：
  19.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  168.01
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-2-Phenethylcarbamoyl-4-[2-(3,4,5-trimethoxy-phenyl)-[1,3]dithian-2-ylmethoxycarbonyloxy]-pyrrolidine-1-carboxylic acid 2,2-dimethoxy-2-(3,4,5-trimethoxy-phenyl)-ethyl ester 在 1,4-环己二烯 、 TEA 、 过碘酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 21.5h， 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
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 1,4-环己二烯 、 (1-azabenzotriazole-1-yloxy)tripyrrolidinophosphonium*BF₆ 、 TEA 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.0h， 生成 (2S,4R)-2-Phenethylcarbamoyl-4-[2-(3,4,5-trimethoxy-phenyl)-[1,3]dithian-2-ylmethoxycarbonyloxy]-pyrrolidine-1-carboxylic acid 2,2-dimethoxy-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