2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose | 299174-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose
• CAS: 299174-88-2
• 化学式: C₅₇H₆₂O₁₂
• 分子量: 939.112
• InChiKey: MLVITGVXSGHJSS-FWICYQLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.33
• 重原子数：
  69.0
• 可旋转键数：
  23.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  110.76
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 在 sodium methylate 、 mercury dibromide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(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 、 (2R,3R,4S,5S,6R)-2-((3aR,5R,6S,7S,7aR)-7-Hydroxy-5-hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose
  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