Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((2S,3R,4S,5R,6R)-6-allyloxy-4,5-dihydroxy-2-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester | 242473-84-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((2S,3R,4S,5R,6R)-6-allyloxy-4,5-dihydroxy-2-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
• CAS: 242473-84-3
• 化学式: C₂₀H₃₀O₁₂
• 分子量: 462.451
• InChiKey: ICBLCZRQUASREV-UMWLAMKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.81
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  156.28
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((2S,3R,4S,5R,6R)-6-allyloxy-4,5-dihydroxy-2-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 在 吡啶 、 2,4-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 4 Angstroem M_.S 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 生成 allyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->2)]-3-O-acetyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  The Regio- and Stereoselective Synthesis of Rhamnose-Containing OligosaccharidesViaSugar-Sugar Orthoester Formation and Rearrangement

  摘要：

  Convenient regio- and stereoselective syntheses of rhamnose-containing oligosaccharides via sugar-sugar orthoester formation and rearrangement are described. 1-->3 Linked rhamno di- and trisaccharides were synthesized effectively using unprotected rhamnose residue as the glycosyl acceptor by this methodology.

  DOI：

  10.1080/07328309908544027
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-α-D-木吡喃糖苷溴 在 4 Angstroem M_.S 、 水 、 silver trifluoromethanesulfonate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((2S,3R,4S,5R,6R)-6-allyloxy-4,5-dihydroxy-2-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  The Regio- and Stereoselective Synthesis of Rhamnose-Containing OligosaccharidesViaSugar-Sugar Orthoester Formation and Rearrangement

  摘要：

  Convenient regio- and stereoselective syntheses of rhamnose-containing oligosaccharides via sugar-sugar orthoester formation and rearrangement are described. 1-->3 Linked rhamno di- and trisaccharides were synthesized effectively using unprotected rhamnose residue as the glycosyl acceptor by this methodology.

  DOI：

  10.1080/07328309908544027