(E)-3-{(2S,3R)-1-[(R)-2,2-Bis-propylsulfanyl-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-3-methoxy-4-oxo-azetidin-2-yl}-acrylic acid benzhydryl ester | 162398-36-9

• 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: (E)-3-{(2S,3R)-1-[(R)-2,2-Bis-propylsulfanyl-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-3-methoxy-4-oxo-azetidin-2-yl}-acrylic acid benzhydryl ester
• CAS: 162398-36-9
• 化学式: C₃₈H₅₁NO₈S₂
• 分子量: 713.957
• InChiKey: HJSOQNZKEKWBOJ-CMKIBRQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  49.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  92.76
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (E)-3-{(2S,3R)-1-[(R)-2,2-Bis-propylsulfanyl-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-3-methoxy-4-oxo-azetidin-2-yl}-acrylic acid benzhydryl ester 在 palladium on activated charcoal 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 作用下， 以 乙醇 、 甲苯 为溶剂， 20.0 ℃ 、131.72 kPa 条件下， 生成 [(2R,3S,4R,5S,6R)-6-Methoxy-7-oxo-3-propylsulfanyl-2-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-aza-bicyclo[3.2.0]hept-4-yl]-acetic acid
  参考文献：
  名称：

  The use of radical decarboxylation in the preparation of 1-methylcarbapenem antibiotic precursors from D-glucosamine

  摘要：

  The stereocontrolled synthesis of optically active 1-methylcarbapenams has been performed by radical cyclization and radical decarboxylation. 1,3,4-Trisubstituted-2-azetidinones, prepared by the Staudinger reaction with D-glucosamine as chiral auxiliary and sorbic acid were used as starting materials.

  DOI：

  10.1016/s0957-4166(00)86289-8
• 作为产物：
  描述：

  oxo-4 butene-2 oate de benzhydryle 在 三乙胺 作用下， 以 甲苯 为溶剂， 生成 (E)-3-{(2S,3R)-1-[(R)-2,2-Bis-propylsulfanyl-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-3-methoxy-4-oxo-azetidin-2-yl}-acrylic acid benzhydryl ester
  参考文献：
  名称：

  The use of radical decarboxylation in the preparation of 1-methylcarbapenem antibiotic precursors from D-glucosamine

  摘要：

  The stereocontrolled synthesis of optically active 1-methylcarbapenams has been performed by radical cyclization and radical decarboxylation. 1,3,4-Trisubstituted-2-azetidinones, prepared by the Staudinger reaction with D-glucosamine as chiral auxiliary and sorbic acid were used as starting materials.

  DOI：

  10.1016/s0957-4166(00)86289-8