(2R,3S)-3-Hydroxy-2-[(2S,3S)-2-hydroxymethyl-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-butyric acid 4-nitro-benzyl ester | 133622-35-2

• 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: (2R,3S)-3-Hydroxy-2-[(2S,3S)-2-hydroxymethyl-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-butyric acid 4-nitro-benzyl ester
• 英文别名: (4-nitrophenyl)methyl (2R,3S)-3-hydroxy-2-[(2S,3S)-2-(hydroxymethyl)-3-(5-nitro-1,3-dioxoisoindol-2-yl)-4-oxoazetidin-1-yl]butanoate
• CAS: 133622-35-2
• 化学式: C₂₃H₂₀N₄O₁₁
• 分子量: 528.432
• InChiKey: GRLOTWQAOVXHMB-NUUCUBOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  216
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-Hydroxy-2-[(2S,3S)-2-hydroxymethyl-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-butyric acid 4-nitro-benzyl ester 在 吡啶 、 chromium(VI) oxide 、 硫酸 、 溴 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 9.67h， 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)-2-[(2S,3S)-2-Formyl-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2R,3S)-3-Hydroxy-2-[(2S,3S)-2-hydroxymethyl-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-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.