O-(Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->2)-O-<(α-L-fucopyranosyl)-(1->3)>-1,5-anhydro-D-glucitol | 176169-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->2)-O-<(α-L-fucopyranosyl)-(1->3)>-1,5-anhydro-D-glucitol
• CAS: 176169-03-2
• 化学式: C₅₉H₇₁NO₂₉
• 分子量: 1258.2
• InChiKey: AFYILXBLLHZGLW-HPDXDVPVSA-N

反应信息

• 作为反应物：
  描述：

  O-(Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->2)-O-<(α-L-fucopyranosyl)-(1->3)>-1,5-anhydro-D-glucitol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 O-(Methyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(β-D-galactopyranosyl-(1->2)-O-[(α-L-fucopyranosyl)-(1->3)]-1,5-anhydro-D-glucitol
  参考文献：
  名称：

  Synthetic Studies on Sialoglycoconjugates 81: Synthesis of Positional Isomers of Sialyl Lewis X Epitope Containing 1-Deoxy-dGlucose in Place ofN-Acetylglucosamine, and Their Inhibitory Activity to Selectin-Mediated Adhesion

  摘要：

  Three sialyl-Le(X) epitope analogs, which carry fucose and alpha-sialyl-(2-->3)galactose residues at O-2 and O-3, O-3 and O-2, and O-4 and O-6 positions of 1-deoxy-D-glucose backbone, respectively, have been synthesized. Glycosylation of 1,5-anhydro-4,6-O-benzylidene-D-glucitol (1) or 1,5-anhydro-6-O-benzoyl-2,3-di-O-benzyl-D-glucitol (4) prepared from 1,5-anhydro-D-glucitol, with methyl 2,3,4-tri-O-benzyl- 1-thio-beta-L-fucopyranoside (5) using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, afforded the corresponding fucosyl 1,5-anhydro-D-glucitol derivatives 7, 8 and 9. Glycosylation of 7, 8 or 10 derived from 9, with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonate)-(2-->3)-2,4,6-tri-O- 1-thio-beta-D-galactopyranoside (11) in the presence of DMTST gave the expected tetrasaccharide derivatives 12, 16 and 20. Hydrolysis of the benzylidene group in 12 and 16 gave compounds 13 and 17. Finally 13, 17 and 20 were transformed, by reductive removal of the benzyl groups, O-deacylation and subsequent hydrolysis of the methyl ester, into the sialyl-Le(X) epitope analogs 15, 19 and 22, respectively.

  DOI：

  10.1080/07328309608005435
• 作为产物：
  描述：

  O-(Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->2)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-1,5-anhydro-D-glucitol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 48.0h， 以83%的产率得到O-(Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->2)-O-<(α-L-fucopyranosyl)-(1->3)>-1,5-anhydro-D-glucitol
  参考文献：
  名称：

  Synthetic Studies on Sialoglycoconjugates 81: Synthesis of Positional Isomers of Sialyl Lewis X Epitope Containing 1-Deoxy-dGlucose in Place ofN-Acetylglucosamine, and Their Inhibitory Activity to Selectin-Mediated Adhesion

  摘要：

  Three sialyl-Le(X) epitope analogs, which carry fucose and alpha-sialyl-(2-->3)galactose residues at O-2 and O-3, O-3 and O-2, and O-4 and O-6 positions of 1-deoxy-D-glucose backbone, respectively, have been synthesized. Glycosylation of 1,5-anhydro-4,6-O-benzylidene-D-glucitol (1) or 1,5-anhydro-6-O-benzoyl-2,3-di-O-benzyl-D-glucitol (4) prepared from 1,5-anhydro-D-glucitol, with methyl 2,3,4-tri-O-benzyl- 1-thio-beta-L-fucopyranoside (5) using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, afforded the corresponding fucosyl 1,5-anhydro-D-glucitol derivatives 7, 8 and 9. Glycosylation of 7, 8 or 10 derived from 9, with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonate)-(2-->3)-2,4,6-tri-O- 1-thio-beta-D-galactopyranoside (11) in the presence of DMTST gave the expected tetrasaccharide derivatives 12, 16 and 20. Hydrolysis of the benzylidene group in 12 and 16 gave compounds 13 and 17. Finally 13, 17 and 20 were transformed, by reductive removal of the benzyl groups, O-deacylation and subsequent hydrolysis of the methyl ester, into the sialyl-Le(X) epitope analogs 15, 19 and 22, respectively.

  DOI：

  10.1080/07328309608005435