[(2S,3R,4S,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyl-2-(4-methylphenyl)sulfanyloxan-3-yl] benzoate | 1415663-25-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyl-2-(4-methylphenyl)sulfanyloxan-3-yl] benzoate
• CAS: 1415663-25-0
• 化学式: C₂₂H₂₇NO₄S
• 分子量: 401.527
• InChiKey: NRRCEZLKYVBBQU-GTVLSUKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  84.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyl-2-(4-methylphenyl)sulfanyloxan-3-yl] benzoate 在 N-碘代丁二酰亚胺 、 2,6-二叔丁基吡啶 、 silver trifluoromethanesulfonate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-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 、 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 、 甲苯 为溶剂， 反应 169.34h， 生成 [(2S,3R,4S,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyl-2-(4-methylphenyl)sulfanyloxan-3-yl] benzoate
  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.