methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside | 131589-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside
• 英文别名: methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-α-D-glucopyranoside；[(2S,3S,4S,5R,6S)-5-benzoyloxy-2-(bromomethyl)-6-methoxy-3-phenylmethoxyoxan-4-yl] benzoate
• CAS: 131589-93-0
• 化学式: C₂₈H₂₇BrO₇
• 分子量: 555.422
• InChiKey: JJWIPZPTRIYECH-MOBZEUQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 对甲苯磺酰氯 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 13.5h， 生成 methyl 4-O-benzyl-6-deoxy-2,3-di-O-p-tolylsulfonyl-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
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 三氯化铝 、 四溴化碳 、 硼烷-三甲胺络合物 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Smith III, Amos B.; Hale, Karl J.; Vaccaro, Henry A., Journal of the American Chemical Society, 1991, vol. 113, # 6, p. 2112 - 2122

  摘要：

  DOI：

文献信息

• The total synthesis of (–)-phyllanthostatin-1
  作者：Amos B. Smith、Karl J. Hale、Henry A. Vaccaro

  DOI：10.1039/c39870001026

  日期：——

  The first total synthesis of the important antitumour glycoside (–)-phyllanthostatin-1 (1) is described; the key steps include a regioselective Koenigs–Knorr reaction to establish the 1,2-O-linkage in disaccharide (6) and a stereoselective triphenylphosphine–di-isopropyl azodicarboxylate (TPP–DIAD) glycosidation of hemiacetal (12) with aglycone (15).

  描述了重要的抗肿瘤糖苷（–）-phyllanthostatin-1（1）的第一个全合成；关键步骤包括在二糖中建立1,2- O区域选择性的Koenigs-Knorr反应（6）和半缩醛（12）与糖苷配基的立体选择性三苯基膦-二异丙基偶氮二羧酸酯（TPP-DIAD）糖基化（15） 。
• 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.
• Smith III, Amos B.; Hale, Karl J.; Vaccaro, Henry A., Journal of the American Chemical Society, 1991, vol. 113, # 6, p. 2112 - 2122
  作者：Smith III, Amos B.、Hale, Karl J.、Vaccaro, Henry A.、Rivero, Ralph A.

  DOI：——

  日期：——