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-α-D-glycero-D-gulo-D-gluco-trideco-1,5-pyranoside | 262293-10-7

• 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-6,7-dideoxy-α-D-glycero-D-gulo-D-gluco-trideco-1,5-pyranoside
• CAS: 262293-10-7
• 化学式: C₅₅H₆₈O₂₂
• 分子量: 1081.13
• InChiKey: DURWXFCUHCGJKZ-YPOCZFESSA-N

物化性质

• 沸点：
  951.1±65.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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-6,7-dideoxy-α-D-glycero-D-gulo-D-gluco-trideco-1,5-pyranoside 在 palladium hydroxide - carbon 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 78.0h， 生成 methyl 8,12-anhydro-6,7-dideoxy-11-O-(β-D-glucopyranosyl)-α-D-glycero-D-gulo-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
• 作为产物：
  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-6,7-dideoxy-7-nitro-α-D-glycero-D-gulo-D-gluco-tridec-6-eno-1,5-pyranoside 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 13.5h， 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-6,7-dideoxy-α-D-glycero-D-gulo-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