methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→3)-2,6-di-O-benzoyl-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→3)-2,6-di-O-benzoyl-β-D-galactopyranoside
• 英文别名: methyl 2,6-di-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-galactopyranoside；Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Gal(b1-3)[Bz(-2)][Bz(-6)]b-Gal1Me；[(2R,3S,4S,5R,6R)-5-benzoyloxy-3-hydroxy-6-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• 化学式: C₅₅H₄₈O₁₇
• 分子量: 980.976
• InChiKey: NHOCRUGBLPNXCD-GIJDWBGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  72
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  215
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→3)-2,6-di-O-benzoyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以100%的产率得到β-D-Galp-(1->3)-β-D-Galp-O-CH3
  参考文献：
  名称：

  Porcine liver (2 → 3)-α-sialyltransferase: substrate specificity studies and application of the immobilized enzyme to the synthesis of various sialylated oligosaccharide sequences

  摘要：

  In search of substrate analogues for the porcine liver beta-D-Galp-(1 --> 3)-D-Galp-NAc: CMP-Neu5Ac-(2 --> 3')-alpha-sialyltransferase, three disaccharides beta-D-Galp-(1 --> 3)-beta-D-Galp-O-CH3 (5), beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-CH3 (7) and beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-Bn (11) were synthesized and tested with the enzyme. Disaccharide 7 turned out to be a very good substrate allowing a rapid access to the trisaccharide alpha-Neu5Ac-(2 --> 3)-beta-D-Galp-(1 --> 3)-P-D-(2-OAc)-Galp-O-CH3 (13) on a preparative scale using the crude enzyme immobilized on cationic exchanger. Trisaccharide 13 was further exploited, first as a sialyl donor in Trypanosoma cruzi trans-sialidase catalyzed reaction and second through acetolysis reaction as a source for the synthon alpha-Neu5Ac-(2 --> 3)-D-Gal (16). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00043-8
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 36.25h， 生成 methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→4)-2,6-di-O-benzoyl-β-D-galactopyranoside 、 methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→3)-2,6-di-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  半乳糖受体糖基化反应的区域选择性：实验和理论研究。

  摘要：

  区域选择性糖基化允许为寡糖的合成规划更简单的策略，从而减少了使用保护基的需要。为了进一步了解这种区域选择性，我们分析了糖基化反应中2，6-二保护的甲基α-和β-吡喃半乳糖苷衍生物的OH-3和OH-4基团的相对反应性。通过简单的方法有效地制备了糖基受体，并评估了具有不同反应性的糖基供体。由于OH-3基团的赤道取向，实现了对1→3产物的高区域选择性。分子建模方法支持了支持O-3取代的总体趋势，尽管它显示出一些无法解释控制某些受体之间区域选择性差异的微妙因素的能力。然而，可以通过使用本文测定的一些受体在区域上选择性地安装Galp-（β1→3）-Galp连接。

  DOI：

  10.3762/bjoc.15.294

文献信息

• Regioselectivity of glycosylation reactions of galactose acceptors: an experimental and theoretical study
  作者：Enrique A Del Vigo、Carlos A Stortz、Carla Marino

  DOI：10.3762/bjoc.15.294

  日期：——

  Regioselective glycosylations allow planning simpler strategies for the synthesis of oligosaccharides, and thus reducing the need of using protecting groups. With the idea of gaining further understanding of such regioselectivity, we analyzed the relative reactivity of the OH-3 and OH-4 groups of 2,6-diprotected methyl α- and β-galactopyranoside derivatives in glycosylation reactions. The glycosyl acceptors

  区域选择性糖基化允许为寡糖的合成规划更简单的策略，从而减少了使用保护基的需要。为了进一步了解这种区域选择性，我们分析了糖基化反应中2，6-二保护的甲基α-和β-吡喃半乳糖苷衍生物的OH-3和OH-4基团的相对反应性。通过简单的方法有效地制备了糖基受体，并评估了具有不同反应性的糖基供体。由于OH-3基团的赤道取向，实现了对1→3产物的高区域选择性。分子建模方法支持了支持O-3取代的总体趋势，尽管它显示出一些无法解释控制某些受体之间区域选择性差异的微妙因素的能力。然而，可以通过使用本文测定的一些受体在区域上选择性地安装Galp-（β1→3）-Galp连接。
• Porcine liver (2 → 3)-α-sialyltransferase: substrate specificity studies and application of the immobilized enzyme to the synthesis of various sialylated oligosaccharide sequences
  作者：André Lubineau、Karine Basset-Carpentier、Claudine Augé

  DOI：10.1016/s0008-6215(97)00043-8

  日期：1997.5

  In search of substrate analogues for the porcine liver beta-D-Galp-(1 --> 3)-D-Galp-NAc: CMP-Neu5Ac-(2 --> 3')-alpha-sialyltransferase, three disaccharides beta-D-Galp-(1 --> 3)-beta-D-Galp-O-CH3 (5), beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-CH3 (7) and beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-Bn (11) were synthesized and tested with the enzyme. Disaccharide 7 turned out to be a very good substrate allowing a rapid access to the trisaccharide alpha-Neu5Ac-(2 --> 3)-beta-D-Galp-(1 --> 3)-P-D-(2-OAc)-Galp-O-CH3 (13) on a preparative scale using the crude enzyme immobilized on cationic exchanger. Trisaccharide 13 was further exploited, first as a sialyl donor in Trypanosoma cruzi trans-sialidase catalyzed reaction and second through acetolysis reaction as a source for the synthon alpha-Neu5Ac-(2 --> 3)-D-Gal (16). (C) 1997 Elsevier Science Ltd.