{(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidin-1-yl}-acetic acid benzyl ester | 828942-68-3

• 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-azetidin-1-yl}-acetic acid benzyl ester
• 英文别名: benzyl 2-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-2-ethenyl-4-oxoazetidin-1-yl]acetate
• CAS: 828942-68-3
• 化学式: C₂₂H₃₃NO₄Si
• 分子量: 403.594
• InChiKey: LQGJNOSBJWQSRR-YVWKXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 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-azetidin-1-yl}-acetic acid benzyl ester 在 (2,5-norbornadiene)Rh⁺B^-Ph₄ 、 chiral binaphthyl-based phosphine ligand 、 氢气 作用下， 以 苯 为溶剂， 60.0 ℃ 、6.08 MPa 条件下， 反应 90.0h， 以100%的产率得到[(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-(3-oxo-propyl)-azetidin-1-yl]-acetic acid benzyl 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
• 作为产物：
  描述：

  (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl-4-vinyl-2-azetidinone] 、 2-溴乙酸苄酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到{(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-vinyl-azetidin-1-yl}-acetic acid benzyl 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

文献信息

• 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
  作者：Edoardo Cesarotti、Isabella Rimoldi

  DOI：10.1016/j.tetasy.2004.10.021

  日期：2004.12

  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.