methyl 9,10,13-tri-O-acetyl-11-O-(tetra-O-acetyl-β-D-glucopyranosyl)-8,12-anhydro-2,3,4-tri-O-benzyl-7-deoxy-7-nitro-α-D-arabino-D-manno-D-gluco-trideco-1,5-pyranoside | 262293-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 9,10,13-tri-O-acetyl-11-O-(tetra-O-acetyl-β-D-glucopyranosyl)-8,12-anhydro-2,3,4-tri-O-benzyl-7-deoxy-7-nitro-α-D-arabino-D-manno-D-gluco-trideco-1,5-pyranoside
• CAS: 262293-07-2
• 化学式: C₅₅H₆₇NO₂₅
• 分子量: 1142.13
• InChiKey: CQNNXNMXFRXBMM-XIKAWYAASA-N

物化性质

• 沸点：
  1013.3±65.0 °C(predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  81.0
• 可旋转键数：
  25.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  321.31
• 氢给体数：
  1.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  methyl 9,10,13-tri-O-acetyl-11-O-(tetra-O-acetyl-β-D-glucopyranosyl)-8,12-anhydro-2,3,4-tri-O-benzyl-7-deoxy-7-nitro-α-D-arabino-D-manno-D-gluco-trideco-1,5-pyranoside 在 吡啶 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 54.0h， 以104.4 mg的产率得到Z-methyl 9,10,13-tri-O-acetyl-11-O-(tetra-O-acetyl-β-D-glucopyranosyl)-8,12-anhydro-2,3,4-tri-O-benzyl-6,7-dideoxy-7-nitro-α-D-glycero-D-gulo-D-gluco-tridec-6-eno-1,5-pyranoside
  参考文献：
  名称：

  The Synthesis of an O,C-Trisaccharide: The O,C-Analog of Methyl 4′-O-β-d-glucopyranosylgentiobioside

  摘要：

  The synthesis of an O,C-trisaccharide, namely methyl O-beta-D-glucopyranosyl-(1-->4)-C-beta-D-glucop glucopyranoside, was achieved in 14 steps by way of the nitro-aldol coupling of hepta-O-acetyl-beta-cellobiosylnitromethane and methyl 6-aldehydo-2,3,4-tri-O-benzyl-alpha-D-gluco-1,5-pyranoside, followed by the elaboration of the coupling product. The resulting O,C-trisaccharide constitutes a potential inhibitor of the beta glucanases of the cellulase family. The perbenzylated derivative of cellobiosyl nitromethane was also prepared. Both disaccharide-C-glycosides constitute useful starting materials for the preparation of higher mixed O,C-oligosaccharides. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00923-0
• 作为产物：
  描述：

  (hepta-O-acetyl-β-D-cellobiosyl)methanol methyldiethylsilyl ether 在 咪唑 、 potassium fluoride 、 间苯三酚 、 18-冠醚-6 、 碘 、 溶剂黄146 、 三苯基膦 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 90.5h， 生成 methyl 9,10,13-tri-O-acetyl-11-O-(tetra-O-acetyl-β-D-glucopyranosyl)-8,12-anhydro-2,3,4-tri-O-benzyl-7-deoxy-7-nitro-α-D-arabino-D-manno-D-gluco-trideco-1,5-pyranoside
  参考文献：
  名称：

  The Synthesis of an O,C-Trisaccharide: The O,C-Analog of Methyl 4′-O-β-d-glucopyranosylgentiobioside

  摘要：

  The synthesis of an O,C-trisaccharide, namely methyl O-beta-D-glucopyranosyl-(1-->4)-C-beta-D-glucop glucopyranoside, was achieved in 14 steps by way of the nitro-aldol coupling of hepta-O-acetyl-beta-cellobiosylnitromethane and methyl 6-aldehydo-2,3,4-tri-O-benzyl-alpha-D-gluco-1,5-pyranoside, followed by the elaboration of the coupling product. The resulting O,C-trisaccharide constitutes a potential inhibitor of the beta glucanases of the cellulase family. The perbenzylated derivative of cellobiosyl nitromethane was also prepared. Both disaccharide-C-glycosides constitute useful starting materials for the preparation of higher mixed O,C-oligosaccharides. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00923-0