2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->3)-5,6-O-isopropylidene-2-O-pivaloyl-D-galactono-1,4-lactone | 440339-55-9

• 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-galactopyranosyl-(1->3)-5,6-O-isopropylidene-2-O-pivaloyl-D-galactono-1,4-lactone
• 英文别名: [(3R,4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-4-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxolan-3-yl] 2,2-dimethylpropanoate
• CAS: 440339-55-9
• 化学式: C₄₈H₅₆O₁₂
• 分子量: 824.965
• InChiKey: UFGPRHYAPSTMSB-PPJGFKFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  60
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->3)-5,6-O-isopropylidene-2-O-pivaloyl-D-galactono-1,4-lactone 在 diisoamyl borane 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->3)-5,6-O-isopropylidene-2-O-pivaloyl-β-D-galactofuranose 、 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->3)-5,6-O-isopropylidene-2-O-pivaloyl-α-D-galactofuranose
  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：

  D-半乳糖酸-1,4-内酯 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 硫酸 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 3.5h， 生成 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->3)-5,6-O-isopropylidene-2-O-pivaloyl-D-galactono-1,4-lactone
  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

文献信息

• Synthesis of α-<scp>d</scp>-Gal<i>p</i>-(1→3)-β-<scp>d</scp>-Gal<i>f</i>-(1→3)-<scp>d</scp>-Man, a Terminal Trisaccharide of <i>Leishmania</i> Type-2 Glycoinositolphospholipids
  作者：Lucia Gandolfi-Donadio、Carola Gallo-Rodriguez、Rosa M. de Lederkremer

  DOI：10.1021/jo016290z

  日期：2002.6.1

  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.