methyl 5-O-p-methoxybenzyl-2,3-O-xylylene-β-D-arabinofuranosyl-(1->2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[5-O-p-methoxybenzyl-2,3-O-xylylene-β-D-arabinofuranosyl-(1->2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-2-O-benzyl-α-D-arabinofuranoside | 1239914-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-O-p-methoxybenzyl-2,3-O-xylylene-β-D-arabinofuranosyl-(1->2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[5-O-p-methoxybenzyl-2,3-O-xylylene-β-D-arabinofuranosyl-(1->2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-2-O-benzyl-α-D-arabinofuranoside
• CAS: 1239914-91-0
• 化学式: C₉₃H₁₀₂O₂₃
• 分子量: 1587.82
• InChiKey: VQLUANZIASFMLQ-IMEOVTRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.04
• 重原子数：
  116.0
• 可旋转键数：
  37.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  212.29
• 氢给体数：
  0.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  methyl 5-O-p-methoxybenzyl-2,3-O-xylylene-β-D-arabinofuranosyl-(1->2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[5-O-p-methoxybenzyl-2,3-O-xylylene-β-D-arabinofuranosyl-(1->2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-2-O-benzyl-α-D-arabinofuranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 以79%的产率得到methyl 2,3-O-xylylene-β-D-arabinofuranosyl-(1->2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[2,3-O-xylylene-β-D-arabinofuranosyl-(1->2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-2-O-benzyl-α-D-arabinofuranoside
  参考文献：
  名称：

  β-Selective Arabinofuranosylation Using a 2,3-O-Xylylene-Protected Donor

  摘要：

  Reported is a novel stereoselective beta-arabinofuranosylation that makes use of a conformationally restricted 2,3-O-zylylene-protected arabinofuranosyl donor. Optimization of the reaction conditions showed that factors including the structure of the acceptor alcohol, substrate concentration, and protecting group on O-5 of the donor affect the stereochemical outcome of the glycosylation. To demonstrate the utility of the methodology, the synthesis of an oligosaccharide fragment from the mycobacterial cell wall polysaccharide lipoarabinomannan was carried out.

  DOI：

  10.1021/ol101520q
• 作为产物：
  描述：

  p-tolyl 5-O-p-methoxybenzyl-1-thio-2,3-O-xylylene-α-D-arabinofuranoside 、 methyl 2-O-benzyl-3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 以65%的产率得到methyl 5-O-p-methoxybenzyl-2,3-O-xylylene-β-D-arabinofuranosyl-(1->2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[5-O-p-methoxybenzyl-2,3-O-xylylene-β-D-arabinofuranosyl-(1->2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-2-O-benzyl-α-D-arabinofuranoside
  参考文献：
  名称：

  β-Selective Arabinofuranosylation Using a 2,3-O-Xylylene-Protected Donor

  摘要：

  Reported is a novel stereoselective beta-arabinofuranosylation that makes use of a conformationally restricted 2,3-O-zylylene-protected arabinofuranosyl donor. Optimization of the reaction conditions showed that factors including the structure of the acceptor alcohol, substrate concentration, and protecting group on O-5 of the donor affect the stereochemical outcome of the glycosylation. To demonstrate the utility of the methodology, the synthesis of an oligosaccharide fragment from the mycobacterial cell wall polysaccharide lipoarabinomannan was carried out.

  DOI：

  10.1021/ol101520q