(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidine-1-carboxylic acid tert-butyl ester | 256371-19-4

• 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: (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-2-ethenyl-4-oxoazetidine-1-carboxylate
• CAS: 256371-19-4
• 化学式: C₁₈H₃₃NO₄Si
• 分子量: 355.55
• InChiKey: CUCHZVMQXGQRLL-MGPQQGTHSA-N

物化性质

• 沸点：
  404.8±38.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidine-1-carboxylic acid tert-butyl ester 在 (2,5-norbornadiene)Rh⁺B^-Ph₄ 、 (S,S)bis(diphenylphosphino)pentane 、 氢气 作用下， 以 苯 为溶剂， 70.0 ℃ 、8.27 MPa 条件下， 反应 24.0h， 生成 (2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-1-methyl-2-oxo-ethyl)-4-oxo-azetidine-1-carboxylic acid tert-butyl ester 、 (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-(3-oxo-propyl)-azetidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of Key 1-Methyl Carbapenem Intermediates via Hydroformylation Using a Zwitterionic Rhodium Catalyst

  摘要：

  The asymmetric hydroformylation of a 4-vinyl beta-lactam catalyzed by a rhodium catalyst with a chiral phosphine ligand was investigated. The catalytic system consisting of a zwitterionic rhodium catalyst, (NBD)Rh+(C6H5B-Ph3) 4, and (S,S)-2,4 bis(diphenylphosphino)pentane, (S,S)-BDPP, gave branched aldehydes in high regio- and stereoselectivity. The hydroformylated products are key intermediates in the synthesis of 1-methylcarbapenem antibiotics. Using (3S,4R)-3-[(R)-1-(tert-butyldimethyl-silyloxy)ethyl]-4-vinyl-2-azetidinone (5a) as the reactant afforded aldehydes in a 97:3 branched-to-linear ratio and 91:9 to beta- to alpha-branched isomers. The regio (branched/linear)- and stereoselectivity (beta/alpha) was >99:1 when (3S,4R)-1-N-BOC-3-[(R)-1-methoxyerhyl]-4-vinyl-2-azetidinone was used as the substrate (5q).

  DOI：

  10.1021/ja993080j
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl-4-vinyl-2-azetidinone] 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以85%的产率得到(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of 1-methylcarbapenem precursors: studies on the diastereoselective hydroformylation of 4-vinyl β-lactam with aminophosphonite–phosphinite and aminophosphine–phosphite rhodium(I) complexes

  摘要：

  The asymmetric hydroformylation of variously N-substituted 4-vinyl beta-lactams catalyzed by rhodium aminophosphonite- phosphinite and rhodium aminophosphine-phosphite complexes was studied. These products are valuable intermediates in the preparation of 1-methylcarbapenem antibiotics; the stereo selectivity to the desired beta-isomer is related to the presence of a substituent at the N atom of the beta-lactain ring. The regioselectivity (branched/linear) but not the stereoselectivity ( beta/alpha) was found to be dependent on the substrate to catalyst ratio. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.10.021