benzyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranosyl-(1→2)-2,3-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside | 1428344-43-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranosyl-(1→2)-2,3-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside
• CAS: 1428344-43-7
• 化学式: C₁₁₂H₁₀₂F₁₀O₂₁
• 分子量: 1974.01
• InChiKey: QLBOPSHKFHXBKD-MSXTVTOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.83
• 重原子数：
  143.0
• 可旋转键数：
  42.0
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  209.51
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  benzyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranosyl-(1→2)-2,3-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 以76%的产率得到benzyl 3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranosyl-(1→2)-2,3-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Backbone Hexasaccharide Fragment of the Pectic Polysaccharide Rhamnogalacturonan I

  摘要：

  Synthesis of the fully unprotected hexasaccharide backbone of the pectic polysaccharide rhamnogalacturonan I is described. The strategy relies on iterative coupling of a common pentenyl disaccharide glycosyl donor followed by a late-stage oxidation of the C-6 positions of the galactose residues. The disaccharide donor is prepared by an efficient chemoselective armed-disarmed coupling of a thiophenyl rhamnoside donor with a pentenyl galactoside acceptor bearing the strongly electron-withdrawing pentafluorobenzoyl ester (PFBz) protective group.

  DOI：

  10.1021/ol400430p
• 作为产物：
  描述：

  pent-4-enyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-Obenzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside 、 benzyl 3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 作用下， 以 甲苯 、 乙醚 为溶剂， 反应 2.0h， 以71%的产率得到benzyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranosyl-(1→2)-2,3-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Backbone Hexasaccharide Fragment of the Pectic Polysaccharide Rhamnogalacturonan I

  摘要：

  Synthesis of the fully unprotected hexasaccharide backbone of the pectic polysaccharide rhamnogalacturonan I is described. The strategy relies on iterative coupling of a common pentenyl disaccharide glycosyl donor followed by a late-stage oxidation of the C-6 positions of the galactose residues. The disaccharide donor is prepared by an efficient chemoselective armed-disarmed coupling of a thiophenyl rhamnoside donor with a pentenyl galactoside acceptor bearing the strongly electron-withdrawing pentafluorobenzoyl ester (PFBz) protective group.

  DOI：

  10.1021/ol400430p