(2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime | 1397274-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime
• CAS: 1397274-90-6
• 化学式: C₁₃H₁₅ClN₂O₈
• 分子量: 362.724
• InChiKey: XMQKSGMJXSWRBA-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  143.88
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 反应 1.0h， 以95%的产率得到(2-chloro-4-nitrophenyl) 6'-deoxy-6'-methoxyamino-β-D-glucopyranoside
  参考文献：
  名称：

  Natural Product Disaccharide Engineering through Tandem Glycosyltransferase Catalysis Reversibility and Neoglycosylation

  摘要：

  A two-step strategy for disaccharide modulation using vancomycin as a model is reported. The strategy relies upon a glycosyltransferase-catalyzed 'reverse' reaction to enable the facile attachment of an alkoxyamine-bearing sugar to the vancomycin core. Neoglycosylation of the corresponding aglycon led to a novel set of vancomycin 1,6-disaccharide variants. While the in vitro antibacterial properties of corresponding vancomycin 1,6-disaccharide analogs were equipotent to the parent antibiotic, the chemoenzymatic method presented is expected to be broadly applicable.

  DOI：

  10.1021/ol3023374
• 作为产物：
  描述：

  2-氯-4-硝基苯酚 在 吡啶 、 咪唑 、 甲醇 、 四丁基溴化铵 、 sodium methylate 、 戴斯-马丁氧化剂 、 乙酰氯 、 sodium hydroxide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 154.0h， 生成 (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime
  参考文献：
  名称：

  Natural Product Disaccharide Engineering through Tandem Glycosyltransferase Catalysis Reversibility and Neoglycosylation

  摘要：

  A two-step strategy for disaccharide modulation using vancomycin as a model is reported. The strategy relies upon a glycosyltransferase-catalyzed 'reverse' reaction to enable the facile attachment of an alkoxyamine-bearing sugar to the vancomycin core. Neoglycosylation of the corresponding aglycon led to a novel set of vancomycin 1,6-disaccharide variants. While the in vitro antibacterial properties of corresponding vancomycin 1,6-disaccharide analogs were equipotent to the parent antibiotic, the chemoenzymatic method presented is expected to be broadly applicable.

  DOI：

  10.1021/ol3023374