N-tert-butoxycarbonyl-D-aspartic acid 4-chloromethyl ester 1-methyl ester | 70606-85-8

• 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: N-tert-butoxycarbonyl-D-aspartic acid 4-chloromethyl ester 1-methyl ester
• 英文别名: N-tert-butoxycarbonyl-D-aspartic acid 4-chloromethyl ester 1-methyl ester
• CAS: 70606-85-8
• 化学式: C₁₁H₁₈ClNO₆
• 分子量: 295.72
• InChiKey: BLCPNLALPVCUPH-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-D-aspartic acid 4-chloromethyl ester 1-methyl ester 在 三氟乙酸 作用下， 反应 2.0h， 生成 L-aspartic acid 4-[(6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyloxymethyl] ester 1-methyl ester
  参考文献：
  名称：

  Orally active esters of cephalosporin antibiotics. 3. Synthesis and biological properties of aminoacyloxymethyl esters of 7-[D-(-)-mandelamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4-carboxylic acid

  摘要：

  The synthesis of six amino acid acyloxymethyl esters of cefamandole (1), a semisynthetic broad-spectrum cephalosporin antibiotic, is described. These esters were examined as potentially useful orally active antibiotic prodrugs. When tested for oral efficacy against Streptococcus pyogenes C203 in mouse protection tests, the esters were not notably more active than lithium cefamandole. Further studies demonstrated that significant blood and urine levels of 1 were not obtained after dosing 2a, 2b, and 2f orally at 17 mg/kg in mice. A study of the stability to chemical hydrolysis and the possible relationship of hydrolysis to the lack of oral absorption of these esters is also presented.

  DOI：

  10.1021/jm00192a010