2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1→3)-1,2,4,6-tetra-O-acetyl-α-D-mannopyranose | 1437790-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1→3)-1,2,4,6-tetra-O-acetyl-α-D-mannopyranose
• CAS: 1437790-30-1
• 化学式: C₂₆H₃₆O₁₇
• 分子量: 620.562
• InChiKey: MBJCCCAEROMHNN-PSRFLFTMSA-N

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1→3)-1,2,4,6-tetra-O-acetyl-α-D-mannopyranose 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以100%的产率得到2,3,4-tri-O-acetyl-α-l-fucopyranosyl-(1→3)-2,4,6-tri-O-acetyl-d-mannopyranose
  参考文献：
  名称：

  Preparation of branched cyclomaltoheptaose with 3-O-α-l-fucopyranosyl-α-d-mannopyranose and changes in fucosylation of HCT116 cells treated with the fucose-modified cyclomaltoheptaose

  摘要：

  From a mixture of 4-nitrophenyl alpha-L-fucopyranoside and D-mannopyranose, 3-O-alpha-L-fucopyranosyl-D-mannopyranose was synthesised through the transferring action of alpha-fucosidase (Sumizyme PHY). 6(I), 6(IV)-Di-O-(3-O-alpha-L-fucopyranosyl-alpha-D-mannopyranosyl)-cyclomaltoheptaose {8, 6(I), 6(IV)-di-O-[alpha-L-Fuc(1 -> 3)-alpha-D-Man]-beta CD} was chemically synthesised using the trichloroacetimidate method. The structures were confirmed by MS and NMR spectroscopy. A cell-based assay using the fucosyl beta CD derivatives, including the newly synthesised 8, showed that derivatives with two branches of the alpha-L-Fuc or alpha-L-Fuc(1 -> 3)-alpha-D-Man residues possessed slight growth-promoting effects and lower toxicity in HCT116 cells compared to those with one branch. These compounds may be useful as drug carriers in targeted drug delivery systems. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.022
• 作为产物：
  描述：

  α-L-fucopyranosyl-(1→3)-D-mannopyranose 、 乙酸酐 在 吡啶 作用下， 以76.2%的产率得到2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1→3)-1,2,4,6-tetra-O-acetyl-α-D-mannopyranose
  参考文献：
  名称：

  Preparation of branched cyclomaltoheptaose with 3-O-α-l-fucopyranosyl-α-d-mannopyranose and changes in fucosylation of HCT116 cells treated with the fucose-modified cyclomaltoheptaose

  摘要：

  From a mixture of 4-nitrophenyl alpha-L-fucopyranoside and D-mannopyranose, 3-O-alpha-L-fucopyranosyl-D-mannopyranose was synthesised through the transferring action of alpha-fucosidase (Sumizyme PHY). 6(I), 6(IV)-Di-O-(3-O-alpha-L-fucopyranosyl-alpha-D-mannopyranosyl)-cyclomaltoheptaose {8, 6(I), 6(IV)-di-O-[alpha-L-Fuc(1 -> 3)-alpha-D-Man]-beta CD} was chemically synthesised using the trichloroacetimidate method. The structures were confirmed by MS and NMR spectroscopy. A cell-based assay using the fucosyl beta CD derivatives, including the newly synthesised 8, showed that derivatives with two branches of the alpha-L-Fuc or alpha-L-Fuc(1 -> 3)-alpha-D-Man residues possessed slight growth-promoting effects and lower toxicity in HCT116 cells compared to those with one branch. These compounds may be useful as drug carriers in targeted drug delivery systems. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.022