(4S,5R,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-3-[1,1-dioxo-7-(2-trifluoromethanesulfonyloxy-ethyl)-1H-1λ⁶-naphtho[1,8-cd]isothiazol-2-ylmethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester | 223740-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S,5R,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-3-[1,1-dioxo-7-(2-trifluoromethanesulfonyloxy-ethyl)-1H-1λ⁶-naphtho[1,8-cd]isothiazol-2-ylmethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
• CAS: 223740-35-0
• 化学式: C₃₁H₃₁F₃N₂O₁₁S₂
• 分子量: 728.721
• InChiKey: YUNAOMODCJVDSB-OPBHZQHKSA-N

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-3-[1,1-dioxo-7-(2-trifluoromethanesulfonyloxy-ethyl)-1H-1λ⁶-naphtho[1,8-cd]isothiazol-2-ylmethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 在 四(三苯基膦)钯 、 5,5-二甲基-1,3-环己二酮 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (4S,5R,6S)-3-[[2,2-dioxo-10-[2-(4-propyl-1,4-diazoniabicyclo[2.2.2]octan-1-yl)ethyl]-2λ6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaen-3-yl]methyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;chloride
  参考文献：
  名称：

  Synthesis and properties of 2-(naphthosultamyl)methyl-carbapenems with potent anti-MRSA activity: Discovery of L-786,392

  摘要：

  A series of 1 beta-methyl-2-(naphthosultamyl)methyl-carbapenems bearing dicationic groups on the naphthosultamyl moiety was prepared and evaluated for activity against resistant gram-positive bacteria. Based on a combination of excellent in vitro antibacterial activity, acceptable mouse acute toxicity, and a desirable fragmentation pattern on beta-lactam ring opening, the analog 2g (L-786,392) was selected for extended evaluation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00071-2
• 作为产物：
  描述：

  三氟甲磺酸酐 、 allyl (1S,5R,6S)-2-(3-(2-(hydroxy)-ethyl-1,8-naphthosultam)methyl)-6-[1(R)-(allyloxycarbonyl)oxyethyl]-1-methylcarbapen-2-em-3-carboxylate 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (4S,5R,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-3-[1,1-dioxo-7-(2-trifluoromethanesulfonyloxy-ethyl)-1H-1λ⁶-naphtho[1,8-cd]isothiazol-2-ylmethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
  参考文献：
  名称：

  Synthesis and properties of 2-(naphthosultamyl)methyl-carbapenems with potent anti-MRSA activity: Discovery of L-786,392

  摘要：

  A series of 1 beta-methyl-2-(naphthosultamyl)methyl-carbapenems bearing dicationic groups on the naphthosultamyl moiety was prepared and evaluated for activity against resistant gram-positive bacteria. Based on a combination of excellent in vitro antibacterial activity, acceptable mouse acute toxicity, and a desirable fragmentation pattern on beta-lactam ring opening, the analog 2g (L-786,392) was selected for extended evaluation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00071-2