methyl 2,3-di-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside | 440339-63-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside
• 英文别名: [(2S,3S,4R,5R)-5-[[(2R,4aR,6S,7S,8R,8aR)-7-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-4-benzoyloxy-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-3-yl] benzoate
• CAS: 440339-63-9
• 化学式: C₃₇H₄₀O₁₃
• 分子量: 692.717
• InChiKey: FWELDGQZVFCNJG-MJGORYESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 methyl β-D-galactofuranosyl-(1->3)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of α-d-Galp-(1→3)-β-d-Galf-(1→3)-d-Man, a Terminal Trisaccharide of Leishmania Type-2 Glycoinositolphospholipids

  摘要：

  The synthesis of alpha-D-Galp-(1-->3)-beta-D-Galf-(1-->3)-D-Man, present in the type-2 glycoinositolphospholipids and in the core of the lipophosphoglycan of Leishmania, is described. The glycosyl aldonolactone approach, followed by reduction of the lactone with diisoamylborane, was utilized for the introduction of the internal galactofuranosyl unit and the trichloroacetimidate method for the O-glycosidation reaction. A high-yield synthesis of the O-D-Galf-(1-->3)-D-Man unit, also present in the lipopeptidophosphoglycan of Trypanosoma cruzi, is reported.

  DOI：

  10.1021/jo016290z
• 作为产物：
  描述：

  methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 、 O-(2,3-di-O-benzoyl-5,6-O-isopropylidene-D-galactofuranosyl)trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以70%的产率得到methyl 2,3-di-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of α-d-Galp-(1→3)-β-d-Galf-(1→3)-d-Man, a Terminal Trisaccharide of Leishmania Type-2 Glycoinositolphospholipids

  摘要：

  The synthesis of alpha-D-Galp-(1-->3)-beta-D-Galf-(1-->3)-D-Man, present in the type-2 glycoinositolphospholipids and in the core of the lipophosphoglycan of Leishmania, is described. The glycosyl aldonolactone approach, followed by reduction of the lactone with diisoamylborane, was utilized for the introduction of the internal galactofuranosyl unit and the trichloroacetimidate method for the O-glycosidation reaction. A high-yield synthesis of the O-D-Galf-(1-->3)-D-Man unit, also present in the lipopeptidophosphoglycan of Trypanosoma cruzi, is reported.

  DOI：

  10.1021/jo016290z