(2S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester | 317385-35-6

• 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: (2S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,5R,6Z)-3,3-dimethyl-6-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethylidene]-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate；tert-butyl (2S,5R,6Z)-3,3-dimethyl-6-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethylidene]-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 317385-35-6
• 化学式: C₁₈H₂₇NO₇S
• 分子量: 401.481
• InChiKey: BWKPVZWWDYAQED-AWQXJLDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester 、 碘甲烷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以23%的产率得到2-{3-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-2-methanesulfonyl-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of antitumor 6-alkylidenepenicillanate sulfones and related 3-alkylidene-2-azetidinones

  摘要：

  6-Alkylidenepenicillanate sulfoxides and sulfones were synthesized on the base of 6-oxopenicillanate esters. The targeted splitting of their thiazolidine ring led to the formation of 3-alkylidene substituted 4-heteryldithio and 4-methylsulfonyl azetidin-2-ones. Some of mono and bicyclic beta-lactams revealed potent cytotoxic properties towards monolayer tumor cells in < 10-muM concentrations. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.078
• 作为产物：
  描述：

  (2S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester 在 间氯过氧苯甲酸 作用下， 以27%的产率得到(2S,5R)-6-[1-tert-Butoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of antitumor 6-alkylidenepenicillanate sulfones and related 3-alkylidene-2-azetidinones

  摘要：

  6-Alkylidenepenicillanate sulfoxides and sulfones were synthesized on the base of 6-oxopenicillanate esters. The targeted splitting of their thiazolidine ring led to the formation of 3-alkylidene substituted 4-heteryldithio and 4-methylsulfonyl azetidin-2-ones. Some of mono and bicyclic beta-lactams revealed potent cytotoxic properties towards monolayer tumor cells in < 10-muM concentrations. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.078