(3S,4R)-1-<(R)-1-<<(p-nitrobenzyl)oxy>carbonyl>-(S)-2-hydroxypropyl>-3-(4-nitrophthalimido)-4-styrylazetidin-2-one | 156767-52-1

• 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)-1-<(R)-1-<<(p-nitrobenzyl)oxy>carbonyl>-(S)-2-hydroxypropyl>-3-(4-nitrophthalimido)-4-styrylazetidin-2-one
• 英文别名: (4-nitrophenyl)methyl (2R,3S)-3-hydroxy-2-[(3S,4R)-3-(5-nitro-1,3-dioxoisoindol-2-yl)-2-oxo-4-[(E)-2-phenylethenyl]azetidin-1-yl]butanoate
• CAS: 156767-52-1
• 化学式: C₃₀H₂₄N₄O₁₀
• 分子量: 600.541
• InChiKey: OUCWSUJCGLZYSE-FRIZLTBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  196
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3S,4R)-1-<(R)-1-<<(p-nitrobenzyl)oxy>carbonyl>-(S)-2-hydroxypropyl>-3-(4-nitrophthalimido)-4-styrylazetidin-2-one 在 吡啶 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 二甲基硫 、 硫酸 、 三氟化硼乙醚 、 溴 、 碳酸氢钠 、 臭氧 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 10.67h， 生成 p-nitrobenzyl (6S,7S)-3-bromomethyl-7-(4-nitrophthalimido)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
  参考文献：
  名称：

  A convenient one pot asymmetric synthesis of cis-β-lactams: Key precursors for optically active 2-oxaisocephems

  摘要：

  Asymmetric annelation of the disilylated imine 3 generated in situ from D-threonine 2 with acid chlorides 4 and triethylamine followed by esterification provided cis-beta-lactams 5 and 6 in excellent yields with high diastereoselectivity under mild conditions. And conversion of compounds 5 into 15, derivatives of 2-oxaisocephems having a thio-substituted methyl group at the 3-position and a 2-aminothiazol-4-yl moiety at the 7-position, is described. Biological activities of the new compounds are presented. In particular, 15b showed potent antibacterial activity against Methicillin-resistant Staphylococcus aureus (MRSA) and Enterococcus faecalis which cause a serious clinical problem in antibacterial chemotherapy.

  DOI：

  10.1016/s0957-4166(00)86216-3
• 作为产物：
  描述：

  (2R,3S)-3-Hydroxy-2-[(3S,4R)-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-4-((E)-styryl)-azetidin-1-yl]-butyric acid 、 对硝基溴化苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (3S,4R)-1-<(R)-1-<<(p-nitrobenzyl)oxy>carbonyl>-(S)-2-hydroxypropyl>-3-(4-nitrophthalimido)-4-styrylazetidin-2-one 、 (2R,3S)-3-Hydroxy-2-[(3R,4S)-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-4-((E)-styryl)-azetidin-1-yl]-butyric acid 4-nitro-benzyl ester
  参考文献：
  名称：

  A convenient one pot asymmetric synthesis of cis-β-lactams: Key precursors for optically active 2-oxaisocephems

  摘要：

  Asymmetric annelation of the disilylated imine 3 generated in situ from D-threonine 2 with acid chlorides 4 and triethylamine followed by esterification provided cis-beta-lactams 5 and 6 in excellent yields with high diastereoselectivity under mild conditions. And conversion of compounds 5 into 15, derivatives of 2-oxaisocephems having a thio-substituted methyl group at the 3-position and a 2-aminothiazol-4-yl moiety at the 7-position, is described. Biological activities of the new compounds are presented. In particular, 15b showed potent antibacterial activity against Methicillin-resistant Staphylococcus aureus (MRSA) and Enterococcus faecalis which cause a serious clinical problem in antibacterial chemotherapy.

  DOI：

  10.1016/s0957-4166(00)86216-3

文献信息

• A convenient one pot asymmetric synthesis of cis-β-lactams: Key precursors for optically active 2-oxaisocephems
  作者：Hidetsugu Tsubouchi、Koichi Tsuji、Koichi Yasumura、Nobuhito Tada、Shinji Nishitani、Jun-ichi Minamikawa、Hiroshi Ishikawa

  DOI：10.1016/s0957-4166(00)86216-3

  日期：1994.3

  Asymmetric annelation of the disilylated imine 3 generated in situ from D-threonine 2 with acid chlorides 4 and triethylamine followed by esterification provided cis-beta-lactams 5 and 6 in excellent yields with high diastereoselectivity under mild conditions. And conversion of compounds 5 into 15, derivatives of 2-oxaisocephems having a thio-substituted methyl group at the 3-position and a 2-aminothiazol-4-yl moiety at the 7-position, is described. Biological activities of the new compounds are presented. In particular, 15b showed potent antibacterial activity against Methicillin-resistant Staphylococcus aureus (MRSA) and Enterococcus faecalis which cause a serious clinical problem in antibacterial chemotherapy.