4-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 717132-47-3

• 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-2,4,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: Bn(-2)[allyl(-3)][Bn(-4)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-Ph(4-OMe)；(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6S)-6-(4-methoxyphenoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-4-prop-2-enoxyoxane
• CAS: 717132-47-3
• 化学式: C₆₄H₆₈O₁₂
• 分子量: 1029.24
• InChiKey: MOIWOYVMXMDWQD-IWGCDCBZSA-N

物化性质

• 熔点：
  80-82 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  76
• 可旋转键数：
  28
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium on activated charcoal 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.5h， 生成 4-methoxyphenyl 2,4,6-tri-O-benzyl-β-D-xylo-hex-3-ulopyranosyl-(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-甲氧苯基-4-O-(β-D-吡喃半乳糖酰基)-β-D-吡喃葡萄糖苷 在 盐酸 、 sodium hydride 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.5h， 生成 4-methoxyphenyl 3-O-allyl-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

文献信息

• Replacement of Carbohydrate Sulfates by Sugar C‐Sulfonic Acid Derivatives
  作者：Anikó Borbás、Magdolna Csávás、László Szilágyi、Gábor Májer、András Lipták

  DOI：10.1081/car-120037571

  日期：2004.12.26

  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.