(5S,6S)-5-((tert-butyldimethylsilyl)oxy)-6-phenylpiperidin-2-one | 1609543-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5S,6S)-5-((tert-butyldimethylsilyl)oxy)-6-phenylpiperidin-2-one
• 英文别名: (5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-6-phenylpiperidin-2-one
• CAS: 1609543-96-5
• 化学式: C₁₇H₂₇NO₂Si
• 分子量: 305.492
• InChiKey: CHYALNJYWHGISC-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5-((tert-butyldimethylsilyl)oxy)-6-phenylpiperidin-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到(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：

  (2R,3S)-3-azido-2-((tert-butyldimethylsilyl)oxy)-3-phenylpropan-1-ol 在 palladium 10% on activated carbon 、 氢气 、 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， 25.0 ℃ 、101.33 kPa 条件下， 反应 16.08h， 生成 (5S,6S)-5-((tert-butyldimethylsilyl)oxy)-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

文献信息

• Optimization and Mechanistic Investigations of Novel Allosteric Activators of PKG1α
  作者：Victor W. Mak、Akash M. Patel、Rose Yen、Jennifer Hanisak、Yeon-Hee Lim、Jianming Bao、Rong Zheng、W. Michael Seganish、Yang Yu、David R. Healy、Aimie Ogawa、Zhao Ren、Aileen Soriano、Grigori P. Ermakov、Maribel Beaumont、Essam Metwally、Alan C. Cheng、Andreas Verras、Thierry Fischmann、Matthias Zebisch、H. Leonardo Silvestre、Paul A. McEwan、John Barker、Paul Rearden、Thomas J. Greshock

  DOI：10.1021/acs.jmedchem.1c02109

  日期：2022.8.11
• 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.