(hepta-O-benzyl-β-D-cellobiosyl)iodomethane | 262293-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (hepta-O-benzyl-β-D-cellobiosyl)iodomethane
• CAS: 262293-17-4
• 化学式: C₆₂H₆₅IO₁₀
• 分子量: 1097.1
• InChiKey: OSPNARNXEOGFSW-XIKNGWJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.66
• 重原子数：
  73.0
• 可旋转键数：
  26.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (hepta-O-benzyl-β-D-cellobiosyl)iodomethane 在 间苯三酚 、 sodium nitrite 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到(hepta-O-benzyl-β-D-cellobiosyl)nitromethane
  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-benzyl-β-D-cellobiosyl)methanol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到(hepta-O-benzyl-β-D-cellobiosyl)iodomethane
  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