2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->5)-2,6-di-O-pivaloyl-D-galactono-1,4-lactone | 606975-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->5)-2,6-di-O-pivaloyl-D-galactono-1,4-lactone
• 英文别名: [(2R)-2-benzoyloxy-2-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-[(1R)-2-(2,2-dimethylpropanoyloxy)-1-[(2R,3S,4R)-4-(2,2-dimethylpropanoyloxy)-3-hydroxy-5-oxooxolan-2-yl]ethoxy]oxolan-2-yl]ethyl] benzoate
• CAS: 606975-63-7
• 化学式: C₅₀H₅₂O₁₇
• 分子量: 924.953
• InChiKey: MAQPUSIGYCADHF-SWWKPXNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  67
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  223
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->5)-2,6-di-O-pivaloyl-D-galactono-1,4-lactone 在 吡啶 、 diisoamyl borane 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 (1R)-1-((2S,3S,4R,5R)-5-((1R)-1-((2S,3S,4R)-3-acetoxy-4-(pivaloyloxy)-5-(2,2,2-trichloro-1-iminoethoxy)tetrahydrofuran-2-yl)-2-(pivaloyloxy)ethoxy)-3,4-bis(benzoyloxy)tetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate
  参考文献：
  名称：

  Syntheses of β-d-Galf-(1→6)-β-d-Galf-(1→5)-d-Galf and β-d-Galf-(1→5)-β-d-Galf-(1→6)-d-Galf, Trisaccharide Units in the Galactan of Mycobacterium tuberculosis

  摘要：

  The galactofuran is a crucial constituent of the cell wall of mycobacteria. An efficient synthesis of the two trisaccharide units of the galactan is described. The strategy relies on the use of substituted D-galactono-1,4-lactones as precursors for the internal and the reducing galactofuranoses. Dec-9-enyl beta-D-Galf-(1-->6)-beta-D-Galf-(1-->5)-beta-D-Galf (2) and dec-9-enyl beta-D-Galf-(1-->5)-beta-D-Galf-(1beta6)-beta-D-Galf (9) so far reported as convenient substrates for the galactofaranosyl transferase, and possibly useful for immunological studies, were obtained by the trichloroacetimidate method of glycosylation.

  DOI：

  10.1021/jo034365o
• 作为产物：
  描述：

  D-半乳糖酸-1,4-内酯 在 吡啶 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 8.17h， 生成 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->5)-2,6-di-O-pivaloyl-D-galactono-1,4-lactone
  参考文献：
  名称：

  Syntheses of β-d-Galf-(1→6)-β-d-Galf-(1→5)-d-Galf and β-d-Galf-(1→5)-β-d-Galf-(1→6)-d-Galf, Trisaccharide Units in the Galactan of Mycobacterium tuberculosis

  摘要：

  The galactofuran is a crucial constituent of the cell wall of mycobacteria. An efficient synthesis of the two trisaccharide units of the galactan is described. The strategy relies on the use of substituted D-galactono-1,4-lactones as precursors for the internal and the reducing galactofuranoses. Dec-9-enyl beta-D-Galf-(1-->6)-beta-D-Galf-(1-->5)-beta-D-Galf (2) and dec-9-enyl beta-D-Galf-(1-->5)-beta-D-Galf-(1beta6)-beta-D-Galf (9) so far reported as convenient substrates for the galactofaranosyl transferase, and possibly useful for immunological studies, were obtained by the trichloroacetimidate method of glycosylation.

  DOI：

  10.1021/jo034365o