(2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide | 141964-95-6

• 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: (2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide
• CAS: 141964-95-6
• 化学式: C₂₀H₃₅NO₅Si
• 分子量: 397.587
• InChiKey: GUFZJPGCPUBMNY-KBAYOESNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide 在 dimethyl azodicarboxylate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以82%的产率得到(3S,4R)-4-Benzyloxymethyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one
  参考文献：
  名称：

  Unique stereocontrol in lanthanide(III)-catalyzed aldol reactions with the ketene silyl acetal of methyl (R)-3-hydroxybutanoate

  摘要：

  The Eu(III)-catalyzed reaction of alpha-benzyloxyaldehydes with the (R)-3-hydroxybutanoate-derived ketene silyl acetal is shown to provide a higher level of both ''anti'' diastereofacial selection and rather unusual anti diastereoselection, compared with the conventional TiCl4-promoted version. The aldol adducts are elaborated to the carbapenem intermediates.

  DOI：

  10.1016/s0040-4039(00)91648-4
• 作为产物：
  描述：

  (2R,3S)-4-Benzyloxy-3-hydroxy-2-((R)-1-hydroxy-ethyl)-butyric acid methyl ester 在 咪唑 、 三甲基铝 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 (2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide
  参考文献：
  名称：

  Unique stereocontrol in lanthanide(III)-catalyzed aldol reactions with the ketene silyl acetal of methyl (R)-3-hydroxybutanoate

  摘要：

  The Eu(III)-catalyzed reaction of alpha-benzyloxyaldehydes with the (R)-3-hydroxybutanoate-derived ketene silyl acetal is shown to provide a higher level of both ''anti'' diastereofacial selection and rather unusual anti diastereoselection, compared with the conventional TiCl4-promoted version. The aldol adducts are elaborated to the carbapenem intermediates.

  DOI：

  10.1016/s0040-4039(00)91648-4