(4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester | 186459-35-8

• 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: (4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (4R,5S,6S)-3-benzylsulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 186459-35-8
• 化学式: C₂₀H₂₃NO₄S
• 分子量: 373.473
• InChiKey: UZGQDWVYKOLRTK-RRCSTGOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 在 palladium diacetate 碳酸氢钠 、 5,5-二甲基-1,3-环己二酮 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以86.9%的产率得到sodium (4R,5S,6S)-3-(benzylthio)-6-((R)-1-hydroxyethyl)-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,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-carboxyethyl]-2-azetidinone 在 4-二甲氨基吡啶 、 氟化铵 、 氢氟酸 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 89.0h， 生成 (4R,5S,6S)-3-Benzylsulfanyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic 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