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-erythro-(L-talo/L-galacto)-D-gluco-trideco-1,5-pyranoside | 262293-09-4

• 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-7-nitro-α-D-erythro-(L-talo/L-galacto)-D-gluco-trideco-1,5-pyranoside
• CAS: 262293-09-4
• 化学式: C₅₅H₆₇NO₂₄
• 分子量: 1126.13
• InChiKey: YLNAKZOTYHKVCE-YGAFQHSGSA-N

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-7-nitro-α-D-erythro-(L-talo/L-galacto)-D-gluco-trideco-1,5-pyranoside 在 palladium hydroxide - carbon 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 乙醇 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.5h， 生成 Acetic acid (2S,3S,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-[2-((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-tetrahydro-pyran-4-yl ester
  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 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 13.0h， 以45%的产率得到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-erythro-(L-talo/L-galacto)-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