2'-carboxybenzyl 2,3-di-O-benzoyl-5-O-levulinyl-α-D-arabinofuranoside | 862163-69-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2'-carboxybenzyl 2,3-di-O-benzoyl-5-O-levulinyl-α-D-arabinofuranoside
• CAS: 862163-69-7
• 化学式: C₃₂H₃₀O₁₁
• 分子量: 590.584
• InChiKey: PEZXUZDLEIOSOX-SIAWKFEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  43.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  151.73
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2'-carboxybenzyl 2,3-di-O-benzoyl-5-O-levulinyl-α-D-arabinofuranoside 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 4 A molecular sieve 、 溶剂黄146 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 methyl [(2,3-di-O-benzoyl-5-O-levulinyl-α-D-arabinofuranosyl)-(1->5)-(2,3-di-O-benzoyl-α-D-arabinofuranosyl)]-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Acceptor-Dependent Stereoselective Glycosylation:  2‘-CB Glycoside-Mediated Direct β-d-Arabinofuranosylation and Efficient Synthesis of the Octaarabinofuranoside in Mycobacterial Cell Wall

  摘要：

  A reliable and generally applicable direct method for the stereoselective beta-arabinofuranosylation employing a 2'-carboxybenzyl arabinofuranoside as the glycosyl donor has been established. The acyl-protective group on glycosyl acceptors is essential for the beta-stereoselectivity. The power of the present acceptor-dependent glycosylation method was demonstrated by the efficient synthesis of the octaarabinofuranoside in arabinogalactan and lipoarabinomannan found in mycobacterial cell wall.

  DOI：

  10.1021/ol0510668
• 作为产物：
  描述：

  2,3-di-O-benzoyl-5-O-levulinyl-α-D-arabinofuranosyl bromide 在 palladium dihydroxide 氢气 、 氰化汞 、 mercury dibromide 作用下， 以 甲醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 0.83h， 生成 2'-carboxybenzyl 2,3-di-O-benzoyl-5-O-levulinyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Acceptor-Dependent Stereoselective Glycosylation:  2‘-CB Glycoside-Mediated Direct β-d-Arabinofuranosylation and Efficient Synthesis of the Octaarabinofuranoside in Mycobacterial Cell Wall

  摘要：

  A reliable and generally applicable direct method for the stereoselective beta-arabinofuranosylation employing a 2'-carboxybenzyl arabinofuranoside as the glycosyl donor has been established. The acyl-protective group on glycosyl acceptors is essential for the beta-stereoselectivity. The power of the present acceptor-dependent glycosylation method was demonstrated by the efficient synthesis of the octaarabinofuranoside in arabinogalactan and lipoarabinomannan found in mycobacterial cell wall.

  DOI：

  10.1021/ol0510668