2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate | 1415663-28-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyltrichloroacetimidate；Bz(-2)[Me2N(-3d)][Bn(-4)]Qui(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-4-(dimethylamino)-6-methyl-5-phenylmethoxy-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 1415663-28-3
• 化学式: C₂₄H₂₇Cl₃N₂O₅
• 分子量: 529.848
• InChiKey: XSMSEOWYPPQCJG-YOQZKJSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate 在 palladium on carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 90.25h， 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 、 三正丁基氢锡 、 sodium methylate 、 乙酸肼 、 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 133.51h， 生成 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate
  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 of 4″-O-desosaminyl clarithromycin derivatives and their anti-bacterial activities
  作者：Di Zhu、Yanpeng Xu、Yi Liu、Xiaozhuo Chen、Zhehui Zhao、Pingsheng Lei

  DOI：10.1016/j.bmcl.2013.09.083

  日期：2013.12

  A series of new 4"-O-desosaminyl clarithromycin derivatives were designed and synthesized. The efficient synthesis routes of 6-deoxy-desosamine donors 8 and 11 were developed and the methodology of glycosylation of clarithromycin 4"-OH with desosamine was studied. The activities of the target compounds were tested against a series of macrolide-sensitive and macrolide-resistant pathogens. Some of them showed activities against macrolide sensitive pathogens, and compounds 19 and 22 displayed significant improvement of activities against sensitive pathogens and two strains of MRSE, which verified the importance of desosamine in the interaction of macrolide and its receptor, and offered valuable information of the SAR of macrolide 4"-OH derivatives. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.