<<3-(benzyloxy)-2,2-dimethylmalonyl>oxy>methyl penicillanate sulfone | 87343-27-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: <<3-(benzyloxy)-2,2-dimethylmalonyl>oxy>methyl penicillanate sulfone
• 英文别名: 3-O-benzyl 1-O-[[(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl] 2,2-dimethylpropanedioate
• CAS: 87343-27-9
• 化学式: C₂₁H₂₅NO₉S
• 分子量: 467.497
• InChiKey: SNFAQCGFUHANPF-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  133.35
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  <<3-(benzyloxy)-2,2-dimethylmalonyl>oxy>methyl penicillanate sulfone 在 palladium on activated charcoal 氢气 、 sodium 2-ethylhexanoic acid 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成 Sodium; 2-((2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyloxymethoxycarbonyl)-2-methyl-propionate
  参考文献：
  名称：

  Orally effective acid prodrugs of the .beta.-lactamase inhibitor sulbactam

  摘要：

  Sulbactam (1) is a beta-lactamase inhibitor with limited oral bioavailability. Lipophilic double-ester prodrug sulbactam pivoxil (2) significantly improves the oral absorption of sulbactam, as does the mutual prodrug double ester sultamicillin (3). We have found that double-ester prodrugs of sulbactam terminating in a carboxyl group (8) also were effective oral-delivery vehicles in rats. Carboxyl-terminated double esters have several potential advantages over their nonionizable lipophilic counterparts, including water solubility, crystallinity, choice of salts for dosage forms, and formation of innocuous byproducts on hydrolysis.

  DOI：

  10.1021/jm00163a055
• 作为产物：
  描述：

  碘甲基舒巴坦 、 tetrabutylammonium benzyl 2,2-dimethylmalonate 以 丙酮 为溶剂， 反应 0.5h， 以52%的产率得到<<3-(benzyloxy)-2,2-dimethylmalonyl>oxy>methyl penicillanate sulfone
  参考文献：
  名称：

  Orally effective acid prodrugs of the .beta.-lactamase inhibitor sulbactam

  摘要：

  Sulbactam (1) is a beta-lactamase inhibitor with limited oral bioavailability. Lipophilic double-ester prodrug sulbactam pivoxil (2) significantly improves the oral absorption of sulbactam, as does the mutual prodrug double ester sultamicillin (3). We have found that double-ester prodrugs of sulbactam terminating in a carboxyl group (8) also were effective oral-delivery vehicles in rats. Carboxyl-terminated double esters have several potential advantages over their nonionizable lipophilic counterparts, including water solubility, crystallinity, choice of salts for dosage forms, and formation of innocuous byproducts on hydrolysis.

  DOI：

  10.1021/jm00163a055

文献信息

• ENGLISH, ARTHUR R.;GIRARD, DENNIS;JASYS, V. JOHN;MARTINGANO, ROBERT J.;KE+, J. MED. CHEM., 33,(1990) N, C. 344-347
  作者：ENGLISH, ARTHUR R.、GIRARD, DENNIS、JASYS, V. JOHN、MARTINGANO, ROBERT J.、KE+

  DOI：——

  日期：——