4-methoxyphenyl 2,6-di-O-benzyl-3-O-(2-naphthyl)methyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 717132-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2,6-di-O-benzyl-3-O-(2-naphthyl)methyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 717132-45-1
• 化学式: C₆₅H₆₆O₁₂
• 分子量: 1039.23
• InChiKey: MXVBUCFFLIDGTN-NMICSLHVSA-N

物化性质

• 熔点：
  131-133 °C(Solvent: Ethyl acetate ; Hexane)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  77.0
• 可旋转键数：
  25.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  121.76
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,6-di-O-benzyl-3-O-(2-naphthyl)methyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 正丁基锂 、 sodium hydride 、 戴斯-马丁氧化剂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 52.25h， 生成 4-methoxyphenyl 3-C-(tetrabutylammonium sulfonate)methyl-β-D-gulopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Replacement of Carbohydrate Sulfates by Sugar C‐Sulfonic Acid Derivatives

  摘要：

  3'-Substituted p-methoxyphenyl beta-lactosides and one of their 3'-epimer were synthesized. The common feature of these compounds is the presence of a strong negative charge at position C-3' in the form of sulfonic acid moieties. The 3',4'-diol derivative of p-methoxyphenyl lactoside was also glycosylated with the thioglycoside of the sulfoulosonic acid. The two-regioisomeric trisaccharides were isolated but their deprotection failed. The aim of the present study was to find carbohydrate ligand(s), which can inhibit the adhesion between Helicobacter pylori and the gastrointestinal epithelial cells.

  DOI：

  10.1081/car-120037571
• 作为产物：
  描述：

  4-methoxyphenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 盐酸 、 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 52.0h， 生成 4-methoxyphenyl 2,6-di-O-benzyl-3-O-(2-naphthyl)methyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Replacement of Carbohydrate Sulfates by Sugar C‐Sulfonic Acid Derivatives

  摘要：

  3'-Substituted p-methoxyphenyl beta-lactosides and one of their 3'-epimer were synthesized. The common feature of these compounds is the presence of a strong negative charge at position C-3' in the form of sulfonic acid moieties. The 3',4'-diol derivative of p-methoxyphenyl lactoside was also glycosylated with the thioglycoside of the sulfoulosonic acid. The two-regioisomeric trisaccharides were isolated but their deprotection failed. The aim of the present study was to find carbohydrate ligand(s), which can inhibit the adhesion between Helicobacter pylori and the gastrointestinal epithelial cells.

  DOI：

  10.1081/car-120037571

文献信息

• Selective removal of the (2-naphthyl)methyl protecting group in the presence of p-methoxybenzyl group by catalytic hydrogenation
  作者：László Lázár、Lóránt Jánossy、Magdolna Csávás、Mihály Herczeg、Anikó Borbása、Sándor Antus

  DOI：10.3998/ark.5550190.0013.526

  日期：——

  Selective cleavage of the (2-naphthyl)methyl (NAP) group in the presence of p-methoxybenzyl (PMB), benzyl and benzylidene groups was achieved by catalytic hydrogenation with a series of monosaccharides. At a disaccharide level, the PMB group was stable upon hydrogenolysis of the NAP, however, partial cleavage of benzyl ether functions was observed.

  在对甲氧基苄基 (PMB)、苄基和亚苄基存在下，(2-萘基)甲基 (NAP) 基团的选择性裂解是通过一系列单糖的催化氢化实现的。在二糖水平上，PMB 基团在 NAP 氢解时是稳定的，但是，观察到苄基醚功能的部分裂解。