phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside | 299174-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
• CAS: 299174-93-9
• 化学式: C₆₂H₆₄O₁₁S
• 分子量: 1017.25
• InChiKey: YADRMGJVYGNKFX-YVBUOIBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.32
• 重原子数：
  74.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  109.37
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 33.0h， 以99%的产率得到phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Prearranged Glycosides, Part 10. Intramolecular Glycosylation with Cellobiosyl, Lactosyl, and Maltosyl Donors

  摘要：

  Acetyl protected 1,2-O-(1-methoxyethylidene)-disaccharides 1 of maltose, cellobiose, and Lactose, respectively were converted via the corresponding benzyl protected couterparts 2, the benzyl protected phenyl 2-O-acetyl-3 and 2-O-unprotected 1-thio-glycoside disaccharides 4 into 2-O-succinoylated disaccharides 5. The latter were esterified with benzyl 2-O-benzoyl-4,6-di-O-benzylidene-alpha-D-glucopyranoside (6) to afford succinyl linked derivatives 7 the benzylidene groups of which were regioselectively opened to give prearranged glycoside trisaccharides 8. Intramolecular glycosylation of the latter with N-iodosuccinimide resulted in exclusive formation of the corresponding alpha-(1-->)-linked trisaccharides 9. No influence of the donor moiety on the diastereoselectivity of the intramolecular glycosylation was observed.

  DOI：

  10.1080/07328300008544113
• 作为产物：
  描述：

  溴甲苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 、 mercury dibromide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成 phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Prearranged Glycosides, Part 10. Intramolecular Glycosylation with Cellobiosyl, Lactosyl, and Maltosyl Donors

  摘要：

  Acetyl protected 1,2-O-(1-methoxyethylidene)-disaccharides 1 of maltose, cellobiose, and Lactose, respectively were converted via the corresponding benzyl protected couterparts 2, the benzyl protected phenyl 2-O-acetyl-3 and 2-O-unprotected 1-thio-glycoside disaccharides 4 into 2-O-succinoylated disaccharides 5. The latter were esterified with benzyl 2-O-benzoyl-4,6-di-O-benzylidene-alpha-D-glucopyranoside (6) to afford succinyl linked derivatives 7 the benzylidene groups of which were regioselectively opened to give prearranged glycoside trisaccharides 8. Intramolecular glycosylation of the latter with N-iodosuccinimide resulted in exclusive formation of the corresponding alpha-(1-->)-linked trisaccharides 9. No influence of the donor moiety on the diastereoselectivity of the intramolecular glycosylation was observed.

  DOI：

  10.1080/07328300008544113

文献信息

• Iron(<scp>iii</scp>) chloride modulated selective 1,2-trans glycosylation based on glycosyl trichloroacetimidate donors and its application in orthogonal glycosylation
  作者：Mana Mohan Mukherjee、Nabamita Basu、Rina Ghosh

  DOI：10.1039/c6ra21859h

  日期：——

  FeCl3 can also modulate the 1,2-trans selectivity of the reaction of 2-O-alkylated gluco- and galacto-pyranosyl trichloroacetimidates with phenolic compounds leading to the generation of the corresponding β-O-aryl glycosides in excellent yield and selectivity. Apart from these the present methodology has been successfully utilized for double glycosylation and orthogonal glycosylation reactions along

  人们已经集中研究了一种新的糖基化方法，该方法可从10摩尔％的FeCl 3介导的相应的三氯乙酰亚氨酸酯供体有效立体选择性合成β-葡萄糖和半乳糖苷。FeCl 3也已应用于许多基于葡萄糖，半乳糖，甘露糖和鼠李糖的三氯乙酰亚氨酸酯供体，这些供体在C-2位置掺入了各种保护基，从而制备了多种具有优异的1,2-反式选择性的二糖和三糖。FeCl 3还可调节2- O反应的1,2-反式选择性-烷基化的葡糖基和半乳糖基-吡喃糖基三氯乙酰亚胺酸酯与酚类化合物的结合，可导致以优异的产率和选择性生成相应的β- O-芳基糖苷。除此之外，本方法已成功地用于双糖基化和正交糖基化反应，以及在三锅合成的一锅三组分正交糖基化反应中的应用。