methyl 2-O-benzoyl-3,5-di-O-benzyl-α-L-arabinofuranoside | 162253-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzoyl-3,5-di-O-benzyl-α-L-arabinofuranoside
• CAS: 162253-39-6
• 化学式: C₂₇H₂₈O₆
• 分子量: 448.516
• InChiKey: OIFZFTKNLYAFIZ-AGBXIKQOSA-N

物化性质

• 沸点：
  569.5±50.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzoyl-3,5-di-O-benzyl-α-L-arabinofuranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以91%的产率得到methyl 3,5-di-O-benzyl-α-L-arabinofuranoside
  参考文献：
  名称：

  Synthesis of regioisomeric methyl α-l-arabinofuranobiosides

  摘要：

  The three regioisomers of methyl alpha-L-arabinofuranobioside, namely methyl O-alpha-L-arabinofuranosyl-(1-->2)-alpha-L-arabinofuranoside, methyl O-alpha-L-arabinofuranosyl-(1-->3)-alpha-L-arabinofuranoside, and methyl O-alpha-L-arabinofuranosyl-(1-->5)-alpha-L-arabinofuranoside, were synthesized for use as substrates in studies of the specificity of alpha-L-arabinofuranosidase. The regiospecifically protected precursors, namely methyl 3,5-di-O-benzoyl-alpha-L-arabinofuranoside, methyl 2,5-di-O-benzyl-alpha-L-arabinofuranoside, and methyl 2,3-di-O-benzoyl-alpha-L-arabinofuranoside, were prepared from 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl chloride (4) and methyl 5-O-trityl-alpha-L-arabinofuranoside, respectively, and glycosylated with 4 in the presence of silver trifluoromethanesulfonate and s-collidine. H-1 and C-13 NMR data for all compounds are presented.

  DOI：

  10.1016/0008-6215(94)00290-v
• 作为产物：
  描述：

  3,5-di-O-benzyl-1,2-(α-methoxybenzylidene)-β-L-arabinofuranose 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到methyl 2-O-benzoyl-3,5-di-O-benzyl-α-L-arabinofuranoside
  参考文献：
  名称：

  Synthesis of regioisomeric methyl α-l-arabinofuranobiosides

  摘要：

  The three regioisomers of methyl alpha-L-arabinofuranobioside, namely methyl O-alpha-L-arabinofuranosyl-(1-->2)-alpha-L-arabinofuranoside, methyl O-alpha-L-arabinofuranosyl-(1-->3)-alpha-L-arabinofuranoside, and methyl O-alpha-L-arabinofuranosyl-(1-->5)-alpha-L-arabinofuranoside, were synthesized for use as substrates in studies of the specificity of alpha-L-arabinofuranosidase. The regiospecifically protected precursors, namely methyl 3,5-di-O-benzoyl-alpha-L-arabinofuranoside, methyl 2,5-di-O-benzyl-alpha-L-arabinofuranoside, and methyl 2,3-di-O-benzoyl-alpha-L-arabinofuranoside, were prepared from 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl chloride (4) and methyl 5-O-trityl-alpha-L-arabinofuranoside, respectively, and glycosylated with 4 in the presence of silver trifluoromethanesulfonate and s-collidine. H-1 and C-13 NMR data for all compounds are presented.

  DOI：

  10.1016/0008-6215(94)00290-v