[(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((R)-1-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid allyl ester | 186459-21-2

• 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,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((R)-1-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid allyl ester
• 英文别名: prop-2-enyl 2-[(3S,4S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-2-oxo-4-[(2R)-1-oxo-1-phenylsulfanylpropan-2-yl]azetidin-1-yl]acetate
• CAS: 186459-21-2
• 化学式: C₂₅H₃₇NO₅SSi
• 分子量: 491.724
• InChiKey: OJVSTCHWSCGLLR-MCEIDBOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((R)-1-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid allyl ester 生成 Allyl (4R,5S,6S)-3-phenylthio-6-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Efficient synthesis of 1β-methylcarbapenems based on the counter-attack strategy

  摘要：

  A seven-step efficient synthesis of 1 beta-methylcarbapenems 1 from the acetoxyazetidinone 6 is described. The Reformatsky reaction of 3-(2-bromopropionyl)-1,3-benzoxazinone 7 with compound 6 gave an adduct 8 in 96% yield with high beta-selectivity (beta:alpha = 92:8). Compound 8 was transformed in three steps into the side-chain thiol esters 12a-e in good yields. The chlorotrimethylsilane-mediated Dieckmann-type cyclisation of thioesters 12b-e followed by counter-attack of the liberated thiolate anion 18 yielded the C-2 alkylthio- or arylthio-substituted 1 beta-methylcarbapenems 19b-e in a one-pot procedure. The synthesis of 1 beta-methylcarbapenems 1 was demonstrated by a simple cleavage of the silyl ether and allyl ester of compound 19b to afford target compound 1b in high yield.

  DOI：

  10.1039/p19960002851
• 作为产物：
  描述：

  (3S,4R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-4-[(1R)-1-[[(tert-butyldimethylsilyl)oxy]carbonyl]ethyl]azetidin-2-one 在 4-二甲氨基吡啶 、 sodium hexamethyldisilazane 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 18.25h， 生成 [(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((R)-1-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid allyl ester
  参考文献：
  名称：

  Efficient synthesis of 1β-methylcarbapenems based on the counter-attack strategy

  摘要：

  A seven-step efficient synthesis of 1 beta-methylcarbapenems 1 from the acetoxyazetidinone 6 is described. The Reformatsky reaction of 3-(2-bromopropionyl)-1,3-benzoxazinone 7 with compound 6 gave an adduct 8 in 96% yield with high beta-selectivity (beta:alpha = 92:8). Compound 8 was transformed in three steps into the side-chain thiol esters 12a-e in good yields. The chlorotrimethylsilane-mediated Dieckmann-type cyclisation of thioesters 12b-e followed by counter-attack of the liberated thiolate anion 18 yielded the C-2 alkylthio- or arylthio-substituted 1 beta-methylcarbapenems 19b-e in a one-pot procedure. The synthesis of 1 beta-methylcarbapenems 1 was demonstrated by a simple cleavage of the silyl ether and allyl ester of compound 19b to afford target compound 1b in high yield.

  DOI：

  10.1039/p19960002851

文献信息

• Efficient synthesis of 1β-methylcarbapenems based on the counter-attack strategy
  作者：Masahiko Seki、Kazuhiko Kondo、Tameo Iwasaki

  DOI：10.1039/p19960002851

  日期：——

  A seven-step efficient synthesis of 1 beta-methylcarbapenems 1 from the acetoxyazetidinone 6 is described. The Reformatsky reaction of 3-(2-bromopropionyl)-1,3-benzoxazinone 7 with compound 6 gave an adduct 8 in 96% yield with high beta-selectivity (beta:alpha = 92:8). Compound 8 was transformed in three steps into the side-chain thiol esters 12a-e in good yields. The chlorotrimethylsilane-mediated Dieckmann-type cyclisation of thioesters 12b-e followed by counter-attack of the liberated thiolate anion 18 yielded the C-2 alkylthio- or arylthio-substituted 1 beta-methylcarbapenems 19b-e in a one-pot procedure. The synthesis of 1 beta-methylcarbapenems 1 was demonstrated by a simple cleavage of the silyl ether and allyl ester of compound 19b to afford target compound 1b in high yield.