2'-(benzyloxycarbonyl)benzyl tri-O-benzyl-α-D-arabinofuranoside | 862163-51-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(benzyloxycarbonyl)benzyl tri-O-benzyl-α-D-arabinofuranoside
• 英文别名: benzyl 2-[[(2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]oxymethyl]benzoate
• CAS: 862163-51-7
• 化学式: C₄₁H₄₀O₇
• 分子量: 644.764
• InChiKey: FRHSQGXHNUSJLM-KSSIXINKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-(benzyloxycarbonyl)benzyl tri-O-benzyl-α-D-arabinofuranoside 在 palladium on activated charcoal 乙酸铵 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 以93%的产率得到2'-carboxybenzyl tri-O-benzyl-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：

  methyl 2,3,5-tri-O-benzyl-D-arabinofuranoside 在 乙酰溴 、 氰化汞 、 三氟乙酸 、 mercury dibromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.5h， 生成 2'-(benzyloxycarbonyl)benzyl tri-O-benzyl-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