methyl 4,6-O-benzylidene-3-O-(3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-2-(4-chlorobenzyl)-β-D-glucopyranoside | 182276-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-O-benzylidene-3-O-(3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-2-(4-chlorobenzyl)-β-D-glucopyranoside
• CAS: 182276-80-8
• 化学式: C₄₁H₄₁ClO₁₂
• 分子量: 761.222
• InChiKey: DBUNKGOBCVIVLX-PLBMDSFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  54.0
• 可旋转键数：
  10.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  129.6
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-3-O-(3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-2-(4-chlorobenzyl)-β-D-glucopyranoside 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 sodium methylate 、 氰化汞 、 mercury dibromide 作用下， 反应 26.0h， 生成
  参考文献：
  名称：

  Synthesis and structural studies of branched 2-linked trisaccharides related to blood group determinants

  摘要：

  A series of trisaccharide glycosides, Fuc-(1 --> 2)-beta-Gal-(1 --> 3)-beta-X-OMe (X = GlcNAc, Glc, 2-deoxy-Glc) related to the blood group determinant Led have been synthesised both as their alpha- and beta-Fuc anomers together with the component disaccharide starting compounds. The conformational properties of the six trisaccharides together with their parent disaccharides have been investigated by NMR spectroscopy (proton and carbon chemical shifts and proton NOEs) in combination with computer modeling using the Monte Carlo approach and the HSEA force field using the GEGOP programme. The interaction between the terminal fucose unit and the reducing unit was probed by substitution of the bulky NAc group with hydroxyl and deoxy substituents, respectively. Compounds with severe steric interactions were identified by the non-additivity of their carbon chemical shifts. This was subsequently confirmed by the detailed conformational assessment by NOE spectroscopy and computer modeling. The most severe contacts arose in the alpha-L-Fuc derivatives, whereas the beta-linked L-Fuc derivatives only in one case exhibit severe steric interaction as probed by the NMR parameters. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0008-6215(96)00103-6
• 作为产物：
  描述：

  在 对甲苯磺酸 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 methyl 4,6-O-benzylidene-3-O-(3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-2-(4-chlorobenzyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and structural studies of branched 2-linked trisaccharides related to blood group determinants

  摘要：

  A series of trisaccharide glycosides, Fuc-(1 --> 2)-beta-Gal-(1 --> 3)-beta-X-OMe (X = GlcNAc, Glc, 2-deoxy-Glc) related to the blood group determinant Led have been synthesised both as their alpha- and beta-Fuc anomers together with the component disaccharide starting compounds. The conformational properties of the six trisaccharides together with their parent disaccharides have been investigated by NMR spectroscopy (proton and carbon chemical shifts and proton NOEs) in combination with computer modeling using the Monte Carlo approach and the HSEA force field using the GEGOP programme. The interaction between the terminal fucose unit and the reducing unit was probed by substitution of the bulky NAc group with hydroxyl and deoxy substituents, respectively. Compounds with severe steric interactions were identified by the non-additivity of their carbon chemical shifts. This was subsequently confirmed by the detailed conformational assessment by NOE spectroscopy and computer modeling. The most severe contacts arose in the alpha-L-Fuc derivatives, whereas the beta-linked L-Fuc derivatives only in one case exhibit severe steric interaction as probed by the NMR parameters. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0008-6215(96)00103-6