[(1S,2R)-1-azido-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropan-2-yl]oxy-tert-butyl-dimethylsilane | 1609543-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1S,2R)-1-azido-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropan-2-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1609543-90-9
• 化学式: C₂₁H₃₉N₃O₂Si₂
• 分子量: 421.731
• InChiKey: PLQPZIAGISFSQT-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.45
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以95%的产率得到(2R,3S)-3-azido-2-((tert-butyldimethylsilyl)oxy)-3-phenylpropan-1-ol
  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：

  rel-(1R,2S)-1-azido-2,3-epoxy-1-phenylpropane 在 咪唑 、 (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III) 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 [(1S,2R)-1-azido-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropan-2-yl]oxy-tert-butyl-dimethylsilane
  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