p-methylphenyl 3-azido-3-deoxy-2,4,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside | 868618-89-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 3-azido-3-deoxy-2,4,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: p-methylphenyl 3-deoxy-3-azido-2,4,6-tri-O-benzoyl-1-thio-D-glucopyranoside
• CAS: 868618-89-7
• 化学式: C₃₄H₂₉N₃O₇S
• 分子量: 623.686
• InChiKey: OTPVUPSNKDRFSY-QRHBHCOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  136.89
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 3-azido-3-deoxy-2,4,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 5.17h， 生成 3-azido-3-deoxy-2,4,6-tri-O-benzoyl-D-glucopyranoside trichloroacetimidate
  参考文献：
  名称：

  An efficient method to synthesize novel 5-O-(6′-modified)-mycaminose 14-membered ketolides

  摘要：

  A new and facile procedure was developed to synthesize novel 5-O-(6'-modified)-mycaminose 14-membered ketolides by adopting different protective strategies and comparing various glycosylation conditions. Seven trichloroacetimidate donors which had different types of substituent groups at C-6 position were synthesized to couple with the erythronolide. Nine novel 5-O-(6'-modified)-mycaminose 14 -membered ketolides were obtained to verify the utility of the method. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.029
• 作为产物：
  描述：

  3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 p-methylphenyl 3-azido-3-deoxy-2,4,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Branched aminoglycosides: Biochemical studies and antibacterial activity of neomycin B derivatives

  摘要：

  The C5"-OH group in neomycin B was glycosylated with a variety of mono- and di-saccharides to probe the effect of introduction of additional binding elements on antibacterial activity and interaction with the aminoglycosides modifying enzyme APH(3')-IIIa. The designed structures show antibacterial activity superior to that of neomycin B against pathogenic and resistant strains, while in parallel they demonstrate poor substrate activity with APH(3')IIIa. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.058