methyl 5-O-benzyl-2,3-O-xylylene-β-D-arabinofuranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside | 1239915-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-O-benzyl-2,3-O-xylylene-β-D-arabinofuranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-2-[[(1R,3R,3aS,11aR)-1-(phenylmethoxymethyl)-1,3,3a,5,10,11a-hexahydrofuro[3,4-c][2,5]benzodioxocin-3-yl]oxymethyl]-4,5-dibenzoyloxy-6-methoxyoxan-3-yl] benzoate
• CAS: 1239915-00-4
• 化学式: C₄₈H₄₆O₁₃
• 分子量: 830.885
• InChiKey: GQQRISURNVWIEC-OZHMZBFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  61
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  甲基2,3,4-三-O-苯甲酰-α-D-吡喃葡萄糖苷 、 p-tolyl 5-O-benzyl-1-thio-2,3-O-xylylene-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 1.5h， 生成 methyl 5-O-benzyl-2,3-O-xylylene-β-D-arabinofuranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 、 methyl 5-O-benzyl-2,3-O-xylylene-α-D-arabinofuranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
  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