(3S,4S)-1-<(R)-1-<(benzhydryloxy)carbonyl>-(S)-2-hydroxypropyl>-4-hydroxymethyl-3-(4-nitrophthalimido)azetidin-2-one | 156662-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4S)-1-<(R)-1-<(benzhydryloxy)carbonyl>-(S)-2-hydroxypropyl>-4-hydroxymethyl-3-(4-nitrophthalimido)azetidin-2-one
• 英文别名: benzhydryl (2R,3S)-3-hydroxy-2-[(2S,3S)-2-(hydroxymethyl)-3-(5-nitro-1,3-dioxoisoindol-2-yl)-4-oxoazetidin-1-yl]butanoate
• CAS: 156662-47-4
• 化学式: C₂₉H₂₅N₃O₉
• 分子量: 559.532
• InChiKey: UNHVYABMKQKXBU-IAHMWCFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  170
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3S,4S)-1-<(R)-1-<(benzhydryloxy)carbonyl>-(S)-2-hydroxypropyl>-4-hydroxymethyl-3-(4-nitrophthalimido)azetidin-2-one 在 吡啶 、 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 乙腈 为溶剂， 反应 6.67h， 生成 (3S,4S)-1-<1-<(benzhydryloxy)carbonyl>-2-hydroxypropenyl>-4-mesyloxymethyl-3-(4-nitrophthalimido)azetidin-2-one
  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：

  (3S,4R)-1-<(R)-1-<(benzhydryloxy)carbonyl>-(S)-2-hydroxypropyl>-3-(4-nitrophthalimido)-4-styrylazetidin-2-one 在 sodium tetrahydroborate 、 二甲基硫 、 三氟化硼乙醚 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (3S,4S)-1-<(R)-1-<(benzhydryloxy)carbonyl>-(S)-2-hydroxypropyl>-4-hydroxymethyl-3-(4-nitrophthalimido)azetidin-2-one
  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