ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate | 1609543-94-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate
• 英文别名: ethyl (E,4S,5S)-5-azido-4-[tert-butyl(dimethyl)silyl]oxy-5-phenylpent-2-enoate
• CAS: 1609543-94-3
• 化学式: C₁₉H₂₉N₃O₃Si
• 分子量: 375.543
• InChiKey: FKKHYWLGFPBFKS-GJAMECAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate 在 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 (5S,6S)-5-hydroxy-6-phenylpiperidin-2-one
  参考文献：
  名称：

  Concise Enantioselective Syntheses of (+)-L-733,060 and (2S,3S)-3-Hydroxypipecolic Acid by Cobalt(III)(salen)-Catalyzed Two-Stereocenter Hydrolytic Kinetic Resolution of Racemic Azido Epoxides

  摘要：

  An efficient synthesis of the 2,3-disubstituted piperidines (+)-L-733,060 and (2S,3S)-3-hydroxypipecolic acid (99% ee) in high optical purity from commercially available starting materials is described. The strategy involves a cobalt-catalyzed hydrolytic kinetic resolution of a racemic azido epoxide with two stereocenters and an intramolecular reductive cyclization as key reactions.

  DOI：

  10.1055/s-0033-1340074
• 作为产物：
  描述：

  [(1S,2R)-1-azido-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropan-2-yl]oxy-tert-butyl-dimethylsilane 在 camphor-10-sulfonic acid 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.08h， 生成 ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate
  参考文献：
  名称：

  Concise Enantioselective Syntheses of (+)-L-733,060 and (2S,3S)-3-Hydroxypipecolic Acid by Cobalt(III)(salen)-Catalyzed Two-Stereocenter Hydrolytic Kinetic Resolution of Racemic Azido Epoxides

  摘要：

  An efficient synthesis of the 2,3-disubstituted piperidines (+)-L-733,060 and (2S,3S)-3-hydroxypipecolic acid (99% ee) in high optical purity from commercially available starting materials is described. The strategy involves a cobalt-catalyzed hydrolytic kinetic resolution of a racemic azido epoxide with two stereocenters and an intramolecular reductive cyclization as key reactions.

  DOI：

  10.1055/s-0033-1340074

文献信息

• Concise Enantioselective Syntheses of (+)-L-733,060 and (2S,3S)-3-Hydroxypipecolic Acid by Cobalt(III)(salen)-Catalyzed Two-Stereocenter Hydrolytic Kinetic Resolution of Racemic Azido Epoxides
  作者：Arumugam Sudalai、Dattatray Devalankar、Pandurang Chouthaiwale

  DOI：10.1055/s-0033-1340074

  日期：——

  An efficient synthesis of the 2,3-disubstituted piperidines (+)-L-733,060 and (2S,3S)-3-hydroxypipecolic acid (99% ee) in high optical purity from commercially available starting materials is described. The strategy involves a cobalt-catalyzed hydrolytic kinetic resolution of a racemic azido epoxide with two stereocenters and an intramolecular reductive cyclization as key reactions.