2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->2)-3,5,6-tri-O-benzoyl-D-galactono-1,4-lactone | 1219003-15-2

• 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-acetyl-β-D-galactopyranosyl-(1->2)-3,5,6-tri-O-benzoyl-D-galactono-1,4-lactone
• CAS: 1219003-15-2
• 化学式: C₄₁H₄₀O₁₈
• 分子量: 820.758
• InChiKey: AXYXGLKXHQAXLB-KXHFZBKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  59.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  228.86
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->2)-3,5,6-tri-O-benzoyl-D-galactono-1,4-lactone 在 bis(2-butyl-3-methyl)borane 作用下， 以 四氢呋喃 为溶剂， 生成 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->2)-3,5,6-tri-O-benzoyl-β-D-galactofuranose 、 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->2)-3,5,6-tri-O-benzoyl-α-D-galactofuranose
  参考文献：
  名称：

  Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins

  摘要：

  The trisaccharides beta-D-Galf-(1 -> 2)-beta-D-Galf-(1 -> 4)-D-GlcNAc (5) and beta-D-Galp-(1 -> 2)-beta-D-Galf-(1 -> 4)-D-GlcNAc (6) constitute novel structures isolated as alditols when released by reductive p-elimination from mucins of Trypanosoma cruzi (Tulahuen strain). Trisaccharides 5 and 6 were synthesized employing the aldonolactone approach. Thus, a convenient D-galactono-1,4-lactone derivative was used for the introduction of the internal galactofuranose and the trichloroacetimidate method was employed for glycosylation reactions. Due to the lack of anchimeric assistance on O-2 of the galactofuranosyl precursor, glycosylation studies were performed under different conditions. The nature of the solvent strongly determined the stereochemical course of the glycosylation reactions when the galactofuranosyl donor was substituted either by 2-O-Galp or 2-O-Galf. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.005
• 作为产物：
  描述：

  3,5,6-tri-O-benzoyl-D-galactono-1,4-lactone 、 2,3,4,6-四-O-乙酰基-Alpha-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以18%的产率得到2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->2)-3,5,6-tri-O-benzoyl-D-galactono-1,4-lactone
  参考文献：
  名称：

  Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins

  摘要：

  The trisaccharides beta-D-Galf-(1 -> 2)-beta-D-Galf-(1 -> 4)-D-GlcNAc (5) and beta-D-Galp-(1 -> 2)-beta-D-Galf-(1 -> 4)-D-GlcNAc (6) constitute novel structures isolated as alditols when released by reductive p-elimination from mucins of Trypanosoma cruzi (Tulahuen strain). Trisaccharides 5 and 6 were synthesized employing the aldonolactone approach. Thus, a convenient D-galactono-1,4-lactone derivative was used for the introduction of the internal galactofuranose and the trichloroacetimidate method was employed for glycosylation reactions. Due to the lack of anchimeric assistance on O-2 of the galactofuranosyl precursor, glycosylation studies were performed under different conditions. The nature of the solvent strongly determined the stereochemical course of the glycosylation reactions when the galactofuranosyl donor was substituted either by 2-O-Galp or 2-O-Galf. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.005