4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranosyl(1->4)-β-D-glucopyranoside | 717132-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranosyl(1->4)-β-D-glucopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-5-[[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-6-(hydroxymethyl)-2-(4-methoxyphenoxy)oxane-3,4-diol
• CAS: 717132-42-8
• 化学式: C₂₂H₃₂O₁₂
• 分子量: 488.489
• InChiKey: SOYXKEQFAHRKBD-ZNQHHCJXSA-N

物化性质

• 熔点：
  222-224 °C(Solvent: Ethanol)
• 沸点：
  730.7±60.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  166
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranosyl(1->4)-β-D-glucopyranoside 在 palladium on activated charcoal 盐酸 、 sodium hydride 、 二正丁基氧化锡 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 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 、 2,2-二甲氧基丙烷 在 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranosyl(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  唾液酸化寡糖的一锅法合成策略

  摘要：

  已经开发出一种使用单锅技术合成支链唾液酸化寡糖的新策略。唾液酸供体的反应性通常太弱而不能用作一锅合成中的第一糖基供体。然而，当唾液酸与不同的糖（如半乳糖）连接时，反应性会显着增强，并且可以进行调整以实现一锅法合成。当使用受阻受体时，NIS??TfOH??AgOTf 的组合用于激活硫糖苷以提高糖基化产率，如唾液酸化六糖的一锅组装所示。 关键词：一锅合成，唾液酸寡糖，新活化。

  DOI：

  10.1139/v02-131

文献信息

• Investigation of glycosylating properties of 1-deoxy-1-ethoxysulfonyl-hept-2-ulopyranosyl derivatives. Synthesis of a new sulfonic acid mimetic of the sialyl Lewis X tetrasaccharide
  作者：Magdolna Csávás、Gábor Májer、Mihály Herczeg、Judit Remenyik、László Lázár、Attila Mándi、Anikó Borbás、Sándor Antus

  DOI：10.1016/j.carres.2011.04.027

  日期：2011.9

  Glycosylation reactions of the ethylthio, bromo and chloro derivatives of 1-deoxy-1-ethoxysulfonyl-hept-2-ulopyranose were studied applying different acceptors under different conditions. Elimination side-reactions affording exo- and endoglycals occured in all cases, however, with different proportions. Glycosyl chloride donor was applied to glycosylate a trisaccharide acceptor obtaining a new sulfonic

  研究了在不同条件下使用不同受体的1-脱氧-1-乙氧基磺酰基-庚-2-铀吡喃糖的乙硫基，溴基和氯基衍生物的糖基化反应。在所有情况下，产生外切糖和内切糖的消除副反应发生的比例不同。糖基氯供体被用于糖基化三糖受体，以高收率获得了新的唾液酸路易斯X四糖的磺酸模拟物。
• A strategy for the one-pot synthesis of sialylated oligosaccharides
  作者：Zhiyuan Zhang、Kenichi Niikura、Xue-Fei Huang、Chi-Huey Wong

  DOI：10.1139/v02-131

  日期：2002.8.1

  A new strategy has been developed for the synthesis of branched sialylated oligosaccharides using one-pot technology. Sialyl donors are in general too weak in reactivity to be used as the first glycosyl donors in the one-pot synthesis. When sialic acid is linked to a different sugar such as galactose, the reactivity is, however, significantly enhanced and can be tuned to enable the one-pot synthesis

  已经开发出一种使用单锅技术合成支链唾液酸化寡糖的新策略。唾液酸供体的反应性通常太弱而不能用作一锅合成中的第一糖基供体。然而，当唾液酸与不同的糖（如半乳糖）连接时，反应性会显着增强，并且可以进行调整以实现一锅法合成。当使用受阻受体时，NIS??TfOH??AgOTf 的组合用于激活硫糖苷以提高糖基化产率，如唾液酸化六糖的一锅组装所示。 关键词：一锅合成，唾液酸寡糖，新活化。
• 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.