o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside | 467219-66-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside
• CAS: 467219-66-5
• 化学式: C₃₇H₃₈O₈S
• 分子量: 642.77
• InChiKey: DPSMLKAWOQVYTB-LPHFZDABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  46.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside 在 palladium dihydroxide 盐酸 、 N-碘代丁二酰亚胺 、 MS 4 Angstroem 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 19.5h， 生成 p-N-acryloylamidophenyl (α-D-galacopyranosyl)-(1->3)-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Convenient use of non-malodorous thioglycosyl donors for the assembly of multivalent globo- and isoglobosyl trisaccharides

  摘要：

  New thioglycosyl donors (o-methoxycarbonylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside and its 6-O-acetyl analogue) were designed and used for the synthesis of glycoconjugate polymers carrying Gb(3) [Gal(alpha1-->4)Gal(beta1-->4)Glc] and isoGb(3) [Gal(alpha1-->3)Gal(beta1-->4)Glc] clusters as side chains. These donors scarcely evolved the unpleasant odor of thiophenols and showed a high alpha-anomeric selectivity in the galactosylation of p-nitrophenyl beta-lactoside derivatives, although in moderate yields. The derived trisaccharides were converted to multivalent carbohydrate ligands and were subjected to a biological assay with Shiga toxins. The multivalent Gb(3) ligand was highly active in inhibiting the toxicity, while the isoGb(3) ligand showed no activity, indicating that Stx-I discriminates between the carbohydrate structures. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00093-9
• 作为产物：
  描述：

  (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium methylate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Convenient use of non-malodorous thioglycosyl donors for the assembly of multivalent globo- and isoglobosyl trisaccharides

  摘要：

  New thioglycosyl donors (o-methoxycarbonylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside and its 6-O-acetyl analogue) were designed and used for the synthesis of glycoconjugate polymers carrying Gb(3) [Gal(alpha1-->4)Gal(beta1-->4)Glc] and isoGb(3) [Gal(alpha1-->3)Gal(beta1-->4)Glc] clusters as side chains. These donors scarcely evolved the unpleasant odor of thiophenols and showed a high alpha-anomeric selectivity in the galactosylation of p-nitrophenyl beta-lactoside derivatives, although in moderate yields. The derived trisaccharides were converted to multivalent carbohydrate ligands and were subjected to a biological assay with Shiga toxins. The multivalent Gb(3) ligand was highly active in inhibiting the toxicity, while the isoGb(3) ligand showed no activity, indicating that Stx-I discriminates between the carbohydrate structures. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00093-9