(3S,4S)-1-<(R)-1-<(benzhydryloxy)carbonyl>-(S)-2-hydroxypropyl>-4-mesyloxymethyl-3-(4-nitrophthalimido)azetidin-2-one | 156662-48-5

• 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,4S)-1-<(R)-1-<(benzhydryloxy)carbonyl>-(S)-2-hydroxypropyl>-4-mesyloxymethyl-3-(4-nitrophthalimido)azetidin-2-one
• CAS: 156662-48-5
• 化学式: C₃₀H₂₇N₃O₁₁S
• 分子量: 637.624
• InChiKey: CQFXMQNAUUHIPH-WFVHXPRMSA-N

物化性质

• 沸点：
  885.0±65.0 °C(predicted)
• 密度：
  1.508±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  190.73
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (3S,4S)-1-<(R)-1-<(benzhydryloxy)carbonyl>-(S)-2-hydroxypropyl>-4-mesyloxymethyl-3-(4-nitrophthalimido)azetidin-2-one 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.67h， 以95%的产率得到(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：

  (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 benzhydryl ester 在 吡啶 、 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 (3S,4S)-1-<(R)-1-<(benzhydryloxy)carbonyl>-(S)-2-hydroxypropyl>-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