cis-3-tert-butyldimethylsilyloxy-4-phenylazetidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: cis-3-tert-butyldimethylsilyloxy-4-phenylazetidin-2-one
• 英文别名: (3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-4-phenylazetidin-2-one
• 化学式: C₁₅H₂₃NO₂Si
• 分子量: 277.439
• InChiKey: XSLAYGYEDULIRR-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  cis-3-tert-butyldimethylsilyloxy-4-phenylazetidin-2-one 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.83h， 生成 2'-epi 3'-epi N-debenzoyl N-tert-butoxycarbonyl taxol
  参考文献：
  名称：

  Synthesis of Docetaxel and Butitaxel Analogues through Kinetic Resolution of Racemic β-Lactams with 7-O-Triethylsilylbaccatin III

  摘要：

  The kinetic resolution of racemic cis-4-phenyl- and cis-4-tert-butyl-3-hydroxy-beta-lactam derivatives with 7-O-triethylsilylbaccatin III yielded paclitaxel and butitaxel analogues with high diastereoselectivity. The results demonstrated that the tert-butyldimethylsilyl protecting group at the C3-hydroxy group of the beta-lactams provided optimum kinetic resolution in comparison with the sterically less demanding triethylsilyl group and the larger triisopropylsilyl group. In addition, it was found that the C4 beta-lactam substituents also influenced diastereoselectivity. The C4 tert-butyl-beta-lactams provided better diastereoselectivity than the corresponding C4 phenyl beta-lactams.

  DOI：

  10.1021/jo061339s
• 作为产物：
  描述：

  (+/-)-cis-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 在 lithium hydroxide 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 8.0h， 生成 cis-3-tert-butyldimethylsilyloxy-4-phenylazetidin-2-one
  参考文献：
  名称：

  Synthesis of Docetaxel and Butitaxel Analogues through Kinetic Resolution of Racemic β-Lactams with 7-O-Triethylsilylbaccatin III

  摘要：

  The kinetic resolution of racemic cis-4-phenyl- and cis-4-tert-butyl-3-hydroxy-beta-lactam derivatives with 7-O-triethylsilylbaccatin III yielded paclitaxel and butitaxel analogues with high diastereoselectivity. The results demonstrated that the tert-butyldimethylsilyl protecting group at the C3-hydroxy group of the beta-lactams provided optimum kinetic resolution in comparison with the sterically less demanding triethylsilyl group and the larger triisopropylsilyl group. In addition, it was found that the C4 beta-lactam substituents also influenced diastereoselectivity. The C4 tert-butyl-beta-lactams provided better diastereoselectivity than the corresponding C4 phenyl beta-lactams.

  DOI：

  10.1021/jo061339s

文献信息

• New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method
  作者：Iwao Ojima、Ivan Habus、Mangzhu Zhao、Martine Zucco、Young Hoon Park、Chung Ming Sun、Thierry Brigaud

  DOI：10.1016/s0040-4020(01)91210-4

  日期：1992.1

  Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs. (3R,4S)-N-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone readily derived from the 3-hydroxy-4-phenyl-β-lactam is coupled

  高效手性酯烯酸酯-亚胺缩合可产生具有优异对映体纯度的3-羟基-4-芳基-β-内酰胺，已成功用于对映体纯紫杉醇C-13侧链N-苯甲酰基-（2 R， 3 S）-3-苯基-异丝氨酸及其类似物。易于衍生自3-羟基-4-苯基-β-内酰胺的（3 R，4 S）-N-苯甲酰基-3-（1-乙氧基乙氧基）-4-苯基-2-氮杂环丁酮与受保护的浆果赤霉素III偶联，然后通过脱保护得到光学纯的紫杉醇和高产率的10-脱乙酰基7,10-双（Troc）-紫杉醇。完全分配的1 H，13显示并讨论了由此合成的紫杉醇的C和2D（COSY和HETCOR）NMR光谱。
• Efficient and practical asymmetric synthesis of the taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogs via chiral 3-hydroxy-4-aryl-.beta.-lactams through chiral ester enolate-imine cyclocondensation
  作者：Iwao Ojima、Ivan Habus、Mangzhu Zhao、Gunda I. Georg、Lalith R. Jayasinghe

  DOI：10.1021/jo00005a003

  日期：1991.3

  A highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-beta-lactams with > 96% ee is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogues.
• Asymmetric Mannich-Type Addition of Lithium Glycolates to Imines Producing 3-Hydroxy-4-phenylazetidin-2-ones
  作者：Kiyoshi Tomioka、Hiroki Fujieda、Seiji Hata、Ken-ichi Yamada

  DOI：10.3987/com-05-s(k)40

  日期：——
• Synthesis of Docetaxel and Butitaxel Analogues through Kinetic Resolution of Racemic β-Lactams with 7-<i>O</i>-Triethylsilylbaccatin III
  作者：Haibo Ge、Jared T. Spletstoser、Yan Yang、Margaret Kayser、Gunda I. Georg

  DOI：10.1021/jo061339s

  日期：2007.2.1

  The kinetic resolution of racemic cis-4-phenyl- and cis-4-tert-butyl-3-hydroxy-beta-lactam derivatives with 7-O-triethylsilylbaccatin III yielded paclitaxel and butitaxel analogues with high diastereoselectivity. The results demonstrated that the tert-butyldimethylsilyl protecting group at the C3-hydroxy group of the beta-lactams provided optimum kinetic resolution in comparison with the sterically less demanding triethylsilyl group and the larger triisopropylsilyl group. In addition, it was found that the C4 beta-lactam substituents also influenced diastereoselectivity. The C4 tert-butyl-beta-lactams provided better diastereoselectivity than the corresponding C4 phenyl beta-lactams.