Carbonic acid (3R,5S)-1-acetyl-5-phenethylcarbamoyl-pyrrolidin-3-yl ester 2-(3,4,5-trimethoxy-phenyl)-[1,3]dithian-2-ylmethyl ester | 828921-16-0

• 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-(3,4,5-trimethoxy-phenyl)-[1,3]dithian-2-ylmethyl ester
• CAS: 828921-16-0
• 化学式: C₃₀H₃₈N₂O₈S₂
• 分子量: 618.772
• InChiKey: URIYJKDGIBRRBF-RPWUZVMVSA-N

物化性质

• 沸点：
  845.9±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112.63
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Carbonic acid (3R,5S)-1-acetyl-5-phenethylcarbamoyl-pyrrolidin-3-yl ester 2-(3,4,5-trimethoxy-phenyl)-[1,3]dithian-2-ylmethyl ester 在 过碘酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以98%的产率得到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：

  2-(3,4,5-trimethoxyphenyl)-1,3-dithiane 在 吡啶 、 4-二甲氨基吡啶 、 1,4-环己二烯 、 (1-azabenzotriazole-1-yloxy)tripyrrolidinophosphonium*BF₆ 、 TEA 、 叔丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 正戊烷 为溶剂， 反应 29.5h， 生成 Carbonic acid (3R,5S)-1-acetyl-5-phenethylcarbamoyl-pyrrolidin-3-yl ester 2-(3,4,5-trimethoxy-phenyl)-[1,3]dithian-2-ylmethyl 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