5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide | 186831-49-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide
• 英文别名: 6-deoxy-L-Tal2Ac3Ac4Ac(a1-2)[Bn(-3)]a-Rhaf1Br5Ac；[(2S,3R,4R,5R,6S)-4,5-diacetyloxy-6-[(2S,3R,4R,5S)-5-[(1S)-1-acetyloxyethyl]-2-bromo-4-phenylmethoxyoxolan-3-yl]oxy-2-methyloxan-3-yl] acetate
• CAS: 186831-49-2
• 化学式: C₂₇H₃₅BrO₁₂
• 分子量: 631.472
• InChiKey: CHRRNTCVWFGMDJ-KTNNUDAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide 在 palladium on activated charcoal molecular sives 3 Angstroem 、 氢气 、 氰化汞 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2R,4R,5R,6S)-5-[(2R,3R,4R,5R)-5-((S)-1-Acetoxy-ethyl)-4-hydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yloxy]-4-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester
  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 2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranoside 在 2,4,6-三甲基吡啶 、 1,1-二氯甲醚 、 silver trifluoromethanesulfonate 、 溴化钛(IV) 、 三氟乙酸 作用下， 生成 5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide
  参考文献：
  名称：

  Banaszek, Anna; Ciunik, Zbigniew, Tetrahedron Letters, 1997, vol. 38, # 2, p. 272 - 276

  摘要：

  DOI：