(2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran | 1202532-50-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran
• CAS: 1202532-50-0
• 化学式: C₆₁H₆₃ClO₁₀
• 分子量: 991.618
• InChiKey: XQMVDPAOFQLNCX-YJBVGCHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.42
• 重原子数：
  72.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以76%的产率得到1,5-anhydro-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-D-arabino-hex-1-enitol
  参考文献：
  名称：

  Ring Expansion of Oxyglycals. Synthesis and Conformational Analysis of Septanoside-Containing Trisaccharides

  摘要：

  Oxyglycals, derived from lactose and maltose, were expanded to trisaccharides through a ring expansion method. Trisaccharides with 6-7-5 and 6-7-6 ring sizes were prepared through the ring expansion method, with high diastereoselectivities, in each step of their synthesis. The NOE and ROESY NMR spectroscopies were used to assess the dipolar Couplings within the trisaccharide. A computational study was undertaken, from which low energy conformations, as well as, dihedral angles that define the glycosidic linkages were identified.

  DOI：

  10.1021/jo901945e
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzyl-α,β-D-glucopyranose 在 氯化亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以84%的产率得到(2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Ring Expansion of Oxyglycals. Synthesis and Conformational Analysis of Septanoside-Containing Trisaccharides

  摘要：

  Oxyglycals, derived from lactose and maltose, were expanded to trisaccharides through a ring expansion method. Trisaccharides with 6-7-5 and 6-7-6 ring sizes were prepared through the ring expansion method, with high diastereoselectivities, in each step of their synthesis. The NOE and ROESY NMR spectroscopies were used to assess the dipolar Couplings within the trisaccharide. A computational study was undertaken, from which low energy conformations, as well as, dihedral angles that define the glycosidic linkages were identified.

  DOI：

  10.1021/jo901945e