(2R,3R,4R)-4-Azidomethyl-3-mercapto-oxetane-2-carboxylic acid methyl ester | 195000-77-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2R,3R,4R)-4-Azidomethyl-3-mercapto-oxetane-2-carboxylic acid methyl ester
• CAS: 195000-77-2
• 化学式: C₆H₉N₃O₃S
• 分子量: 203.222
• InChiKey: KPSDMOXEQZLQAA-MROZADKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.54
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.29
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-4-Azidomethyl-3-mercapto-oxetane-2-carboxylic acid methyl ester 在 palladium on activated charcoal i-PrNEt 、 氢气 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成 (4R,5S,6S)-3-[(2R,3R,4R)-2-(aminomethyl)-4-methoxycarbonyloxetan-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of some novel oxetane carbapenems

  摘要：

  Six disubstituted oxetane carbapenems were synthesized and their antibacterial profile compared with the lead amino methyl THF carbapenem as well as imipenem. The oxetane carbapenems had comparable or less activity against the Gram(-) bacteria and had reduced activity against Gram(+) bacteria in comparison with imipenem and the THF carbapenem CL 191,121, but were highly stable to hydrolysis by hog kidney dehydropeptidase (DHP). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00280-1
• 作为产物：
  描述：

  (2R,3R,4R)-3-Acetylsulfanyl-4-(tert-butyl-diphenyl-silanyloxymethyl)-oxetane-2-carboxylic acid methyl ester 在 吡啶 、 叠氮化锂 、 四丁基氟化铵 、 溶剂黄146 作用下， 生成 (2R,3R,4R)-4-Azidomethyl-3-mercapto-oxetane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of some novel oxetane carbapenems

  摘要：

  Six disubstituted oxetane carbapenems were synthesized and their antibacterial profile compared with the lead amino methyl THF carbapenem as well as imipenem. The oxetane carbapenems had comparable or less activity against the Gram(-) bacteria and had reduced activity against Gram(+) bacteria in comparison with imipenem and the THF carbapenem CL 191,121, but were highly stable to hydrolysis by hog kidney dehydropeptidase (DHP). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00280-1