p-methylphenyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside | 1415663-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5S,6R)-4-(dimethylamino)-6-methyl-2-(4-methylphenyl)sulfanyl-5-phenylmethoxyoxan-3-yl] benzoate
• CAS: 1415663-24-9
• 化学式: C₂₉H₃₃NO₄S
• 分子量: 491.651
• InChiKey: CRBUFKPABYGKKI-BHRGRCPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  73.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 2,6-二叔丁基吡啶 、 palladium on carbon 、 氢气 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 88.0h， 生成 3-O-descladinosyl-6-O-methyl-5-mycaminosyl-3-oxo-erythronolide A 11,12-cyclic carbonate
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel modified 5-O-desosamine ketolides

  摘要：

  A series of novel modified 5-O-desosamine-ketolides were synthesized. The 5-O-desosamine fragment was removed from ketolide by an efficient and mild manipulation. 4-O-substituted desosamine was introduced into the ketolide aglycon and various coupling methods were essayed for the glycosylation. Three novel ketolides were tested for in vitro antibacterial activity against a panel of susceptible and resistant pathogens. Compound 26 showed potent activity against all the methicillin-sensitivity and resistant pathogens. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.064
• 作为产物：
  描述：

  methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 偶氮二异丁腈 、 四溴化碳 、 硫酸 、 三氟化硼乙醚 、 三正丁基氢锡 、 sodium methylate 、 sodium hydride 、 溶剂黄146 、 对甲苯磺酰氯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 172.34h， 生成 p-methylphenyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel modified 5-O-desosamine ketolides

  摘要：

  A series of novel modified 5-O-desosamine-ketolides were synthesized. The 5-O-desosamine fragment was removed from ketolide by an efficient and mild manipulation. 4-O-substituted desosamine was introduced into the ketolide aglycon and various coupling methods were essayed for the glycosylation. Three novel ketolides were tested for in vitro antibacterial activity against a panel of susceptible and resistant pathogens. Compound 26 showed potent activity against all the methicillin-sensitivity and resistant pathogens. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.064

文献信息

• Synthesis and antibacterial activity of novel modified 5-O-desosamine ketolides
  作者：Xiaozhuo Chen、Peng Xu、Yanpeng Xu、Lu Liu、Yi Liu、Di Zhu、Pingsheng Lei

  DOI：10.1016/j.bmcl.2012.10.064

  日期：2012.12

  A series of novel modified 5-O-desosamine-ketolides were synthesized. The 5-O-desosamine fragment was removed from ketolide by an efficient and mild manipulation. 4-O-substituted desosamine was introduced into the ketolide aglycon and various coupling methods were essayed for the glycosylation. Three novel ketolides were tested for in vitro antibacterial activity against a panel of susceptible and resistant pathogens. Compound 26 showed potent activity against all the methicillin-sensitivity and resistant pathogens. (C) 2012 Elsevier Ltd. All rights reserved.