(3S,4R)-3-(2'-bromo-1'-oxoethyl)-1-(tert-butyldimethylsilyl)-4-<1'(R)-methyl-3'-<(allyloxy)carbonyl>-2'-oxo-3'-diazopropyl>azetidin-2-one | 138898-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4R)-3-(2'-bromo-1'-oxoethyl)-1-(tert-butyldimethylsilyl)-4-<1'(R)-methyl-3'-<(allyloxy)carbonyl>-2'-oxo-3'-diazopropyl>azetidin-2-one
• 英文别名: (3S,4R)-3-(2'-bromo-1'-oxoethyl)-1-(tert-butyldimethylsilyl)-4-{1'(R)-methyl-3'-[(allyloxy)carbonyl]-2'-oxo-3'-diazopropyl}azetidin-2-one；(Z,4R)-4-[(2R,3S)-3-(2-bromoacetyl)-1-[tert-butyl(dimethyl)silyl]-4-oxoazetidin-2-yl]-2-diazonio-3-oxo-1-prop-2-enoxypent-1-en-1-olate
• CAS: 138898-94-9
• 化学式: C₁₉H₂₈BrN₃O₅Si
• 分子量: 486.438
• InChiKey: ZYGHXHDMPOPSGW-UXIGCNINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  117.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-(2'-bromo-1'-oxoethyl)-1-(tert-butyldimethylsilyl)-4-<1'(R)-methyl-3'-<(allyloxy)carbonyl>-2'-oxo-3'-diazopropyl>azetidin-2-one 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (R)-4-[(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-(S)-oxiranyl-4-oxo-azetidin-2-yl]-2-diazo-3-oxo-pentanoic acid allyl ester
  参考文献：
  名称：

  The synthesis of an asparenomycin analog

  摘要：

  The synthesis of an analog of the carbapenem antibiotics, the asparenomycins, is described. This analog lacks the methyl group in the 6-alkylidene side chain while a methyl group has been placed at the 1-beta-position. The key step involved the Lewis acid-catalyzed rearrangement of an epoxide to an allylic alcohol.

  DOI：

  10.1016/s0040-4039(00)74477-7
• 作为产物：
  描述：

  (R)-4-((2R,3S)-3-Acetyl-4-oxo-azetidin-2-yl)-2-diazo-3-oxo-pentanoic acid allyl ester 在 溴 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3S,4R)-3-(2'-bromo-1'-oxoethyl)-1-(tert-butyldimethylsilyl)-4-<1'(R)-methyl-3'-<(allyloxy)carbonyl>-2'-oxo-3'-diazopropyl>azetidin-2-one
  参考文献：
  名称：

  The synthesis of an asparenomycin analog

  摘要：

  The synthesis of an analog of the carbapenem antibiotics, the asparenomycins, is described. This analog lacks the methyl group in the 6-alkylidene side chain while a methyl group has been placed at the 1-beta-position. The key step involved the Lewis acid-catalyzed rearrangement of an epoxide to an allylic alcohol.

  DOI：

  10.1016/s0040-4039(00)74477-7

文献信息

• Synthesis and antibacterial activity of some novel 6-methyl- and 6-propenyl-substituted carbapenems
  作者：Harold Mastalerz、Marcel Menard、Edward Ruediger、Joan Fung-Tomc

  DOI：10.1021/jm00083a022

  日期：1992.3

  The synthesis and antibacterial activity of a number of 6-methyl- and 6-propenyl-substituted carbapenems is described. The 6-(hydroxymethyl)- and 6-(aminomethyl)carbapenems possessed more potent antibacterial activity in vitro than their respective 6-(1'(R)-hydroxyethyl) or 6-(1'(R)-aminoethyl) counterparts. However, because of reduced stability, the 6-(aminomethyl)carbapenem was found to be inactive

  描述了许多6-甲基和6-丙烯基取代的碳青霉烯的合成和抗菌活性。与它们各自的6-（1'（R）-羟乙基）或6-（1'（R）-氨基乙基）对应物相比，6-（羟甲基）-和6-（氨基甲基）咔啉具有更强的体外抗菌活性。然而，由于降低的稳定性，发现6-（氨基甲基）卡巴培南在体内无活性。所制备的所有6-羟基丙烯基或6-氨基丙烯基衍生物的活性均低于其各自的6-杂乙基取代的类似物。