methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside | 1415663-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5S,6R)-4-(dimethylamino)-2-methoxy-6-methyl-5-phenylmethoxyoxan-3-yl] benzoate
• CAS: 1415663-21-6
• 化学式: C₂₃H₂₉NO₅
• 分子量: 399.487
• InChiKey: WPSJKMQUQBEXBO-YPCMALBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 2,6-二叔丁基吡啶 、 硫酸 、 三氟化硼乙醚 、 silver trifluoromethanesulfonate 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 99.0h， 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 、 三正丁基氢锡 、 sodium methylate 、 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 73.34h， 生成 methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-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-mycaminose 14-membered ketolides
  作者：Yanpeng Xu、Xiaozhuo Chen、Di Zhu、Yi Liu、Zhehui Zhao、Longlong Jin、Chao Liu、Pingsheng Lei

  DOI：10.1016/j.ejmech.2013.08.023

  日期：2013.11

  A practicable method of introducing a side chain to the C-4' position of 5-O-desosamine in the 14membered ketolides was developed. And using this method, a series of novel modified 5-O-mycaminose ketolides were synthesized. These ketolides containing 5-O-4'-carbamate mycaminose were evaluated for their in vitro antibacterial activities against some respiratory pathogens. 15b and 18e showed comparable activity to telithromycin and clarithromycin. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis of several novel 14-membered ketolides bearing modified 5-O-4′-[1,2,3] triazol desosamine side chain
  作者：Xiaozhuo Chen、Yanpeng Xu、Zhehui Zhao、Pingsheng Lei

  DOI：10.1016/j.tetlet.2014.09.064

  日期：2014.10

  4-Azido modified desosamine 4a was synthesized and coupled to erythronolide 9. Using trichloroacetimidate donor in the presence of TMSOTf was considered as the most efficient condition for the glycosylation reaction. Five novel 14-membered ketolides 12a-e bearing modified 5-O-4'-[1,2,3] triazol desosamine side chain were synthesized by the azide/alkyne click chemistry method. (C) 2014 Elsevier Ltd. All rights reserved.
• 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.