5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate | 1415663-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate
• CAS: 1415663-31-8
• 化学式: C₃₈H₅₇NO₁₂
• 分子量: 719.87
• InChiKey: KDVKPSPDGPRHSP-SMARVDAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  51.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  156.36
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate 在 palladium on carbon 、 氢气 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 以68%的产率得到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 4-O-benzyl-6-deoxy-2,3-di-O-p-tolylsulfonyl-α-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 硫酸 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 206.17h， 生成 5-(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