2-O-(2,3,4-tri-acetyl-6-deoxy-α-L-talopyranosyl)-3,4-di-O-acetyl-α-L-rhamnopyranose | 210048-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-(2,3,4-tri-acetyl-6-deoxy-α-L-talopyranosyl)-3,4-di-O-acetyl-α-L-rhamnopyranose
• CAS: 210048-40-1
• 化学式: C₂₂H₃₂O₁₄
• 分子量: 520.488
• InChiKey: YGKWSQCAUPYMHP-MDBXOWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  179.42
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2-O-(2,3,4-tri-acetyl-6-deoxy-α-L-talopyranosyl)-3,4-di-O-acetyl-α-L-rhamnopyranose 在 palladium on activated charcoal 3 A molecular sieve 、 三氟化硼乙醚 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.42h， 生成
  参考文献：
  名称：

  Synthesis of the unique trisaccharide repeating unit, isolated from lipopolysaccharides Rhizobium leguminosarum bv. trifolii 24, and its analogue

  摘要：

  The synthesis of trisaccharide: 6-d-alpha-L-Talp(1-->2)-alpha-L-Rhap(1-->5)-DHA, and its analogue: 6-d-alpha-L-Talp(1-->2)-beta-L-Rhaf(1-->5)DHA is described. In the first step a disaccharide, composed of 6-d-L-Talp and L-Rhap was obtained. This, in turn, was converted to the corresponding 1-trichloroacetimidate and coupled with DHA alcohol to afford the required trisaccharide. Its analogue was achieved by the conversion of the above disaccharide to the glycosyl bromide, involving the rhamnopyranose ring scission, followed by condensation with DHA in Koenigs-Knorr procedure. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)10073-8
• 作为产物：
  描述：

  t-butyl 3,4-di-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnopyranoside 在 palladium on activated charcoal 三氟乙酸 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-O-(2,3,4-tri-acetyl-6-deoxy-α-L-talopyranosyl)-3,4-di-O-acetyl-α-L-rhamnopyranose
  参考文献：
  名称：

  Synthesis of the unique trisaccharide repeating unit, isolated from lipopolysaccharides Rhizobium leguminosarum bv. trifolii 24, and its analogue

  摘要：

  The synthesis of trisaccharide: 6-d-alpha-L-Talp(1-->2)-alpha-L-Rhap(1-->5)-DHA, and its analogue: 6-d-alpha-L-Talp(1-->2)-beta-L-Rhaf(1-->5)DHA is described. In the first step a disaccharide, composed of 6-d-L-Talp and L-Rhap was obtained. This, in turn, was converted to the corresponding 1-trichloroacetimidate and coupled with DHA alcohol to afford the required trisaccharide. Its analogue was achieved by the conversion of the above disaccharide to the glycosyl bromide, involving the rhamnopyranose ring scission, followed by condensation with DHA in Koenigs-Knorr procedure. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)10073-8