α-L-rhamnopyranosyl-(1→4)-(α-D-galactopyranosyluronic acid)-(1→2)-α-Lrhamnopyranosyl-(1→4)-(α-D-galactopyranosyluronic acid)-(1→2)-α-L-rhamnopyranosyl-(1→4)-D-galactopyranosiduronic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-L-rhamnopyranosyl-(1→4)-(α-D-galactopyranosyluronic acid)-(1→2)-α-Lrhamnopyranosyl-(1→4)-(α-D-galactopyranosyluronic acid)-(1→2)-α-L-rhamnopyranosyl-(1→4)-D-galactopyranosiduronic acid
• 英文别名: Rha(a1-4)GalA(a1-2)Rha(a1-4)GalA(a1-2)Rha(a1-4)GalA；(2S,3R,4R,5R)-3-[(2S,3R,4R,5R,6S)-3-[(2S,3R,4R,5R,6S)-6-carboxy-5-[(2S,3R,4R,5R,6S)-3-[(2S,3R,4R,5R,6S)-6-carboxy-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid
• 化学式: C₃₆H₅₆O₃₁
• 分子量: 984.822
• InChiKey: KPBHOMHWGZCLNM-KBAKPNJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10
• 重原子数：
  67
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  497
• 氢给体数：
  17
• 氢受体数：
  31

反应信息

• 作为产物：
  描述：

  benzyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-(benzyl 2,3-di-O-benzyl-α-D-galactopyranosyluronate)-(1→2)-2,3-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-(benzyl 2,3-di-O-benzyl-α-D-galactopyranosyluronate)-(1→2)-2,3-di-O-benzyl-α-Lrhamnopyranosyl-(1→4)-(benzyl 2,3-di-O-benzyl-α-D-galactopyranosiduronate) 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以95%的产率得到α-L-rhamnopyranosyl-(1→4)-(α-D-galactopyranosyluronic acid)-(1→2)-α-Lrhamnopyranosyl-(1→4)-(α-D-galactopyranosyluronic acid)-(1→2)-α-L-rhamnopyranosyl-(1→4)-D-galactopyranosiduronic acid
  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