4-methoxyphenyl 3-O-allyl-2,6-di-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 717132-44-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 3-O-allyl-2,6-di-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 717132-44-0
• 化学式: C₅₇H₆₂O₁₂
• 分子量: 939.112
• InChiKey: PPDCLRCJCXEIRX-ZEAHIQBJSA-N

物化性质

• 熔点：
  102-104 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  956.3±65.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.03
• 重原子数：
  69.0
• 可旋转键数：
  25.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 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 3-O-allyl-2,6-di-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium on activated charcoal sodium hydride 、 对甲苯磺酸 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 4-methoxyphenyl 2,4,6-tri-O-benzyl-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
• 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 3-O-allyl-2,6-di-O-benzyl-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

• Boronic Acid/Palladium Hybrid Catalysis for Regioselective <i>O</i>-Allylation of Carbohydrates
  作者：Yuki Nakamura、Kazuma Irisawa、Kazuishi Makino、Naoyuki Shimada

  DOI：10.1021/acs.joc.3c02445

  日期：2024.1.19

  Novel imidazole-containing boronic acid and palladium hybrid catalysis for regioselective O-allylation of carbohydrates has been developed. This catalytic process enables the introduction of a useful allyl functional group into the equatorial hydroxy group of cis-1,2-diols of various carbohydrates with low catalyst loading and excellent regioselectivities. This is the first report on hybrid catalysis

  已经开发出用于碳水化合物区域选择性O-烯丙基化的新型含咪唑硼酸和钯杂化催化。该催化过程能够将有用的烯丙基官能团引入各种碳水化合物的顺式-1,2-二醇的赤道羟基中，并具有低催化剂负载量和优异的区域选择性。这是关于含路易斯碱的硼酸和过渡金属络合物的混合催化的第一份报告。