p-methoxyphenyl [4-O-acetyl-3,6-di-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1→3)-4-O-benzoyl-2-O-benzyl-α-L-fucopyranoside | 1607433-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl [4-O-acetyl-3,6-di-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1→3)-4-O-benzoyl-2-O-benzyl-α-L-fucopyranoside
• 英文别名: Mob(-2)[Bn(-3)][Bn(-6)]Gal4Ac(a1-3)[Bn(-2)][Bz(-4)]Fuc(a)-O-Ph(4-OMe)；[(2S,3R,4R,5S,6S)-4-[(2R,3R,4S,5S,6R)-5-acetyloxy-3-[(4-methoxyphenyl)methoxy]-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-(4-methoxyphenoxy)-2-methyl-5-phenylmethoxyoxan-3-yl] benzoate
• CAS: 1607433-80-6
• 化学式: C₅₇H₆₀O₁₄
• 分子量: 969.095
• InChiKey: DJLWYUCPGIKCHP-GMLDVVGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.07
• 重原子数：
  71.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  144.9
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl [4-O-acetyl-3,6-di-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1→3)-4-O-benzoyl-2-O-benzyl-α-L-fucopyranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 aq. phosphate buffer 、 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到p-methoxyphenyl (4-O-acetyl-3,6-di-O-benzyl-α-D-galactopyranosyl)-(1→3)-4-O-benzoyl-2-O-benzyl-α-L-fucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from Sargassum polycystum

  摘要：

  The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed D-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.

  DOI：

  10.1021/jo500503r
• 作为产物：
  描述：

  4-methoxyphenyl α-L-fucopyranoside 在 盐酸 、 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.0h， 生成 p-methoxyphenyl [4-O-acetyl-3,6-di-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1→3)-4-O-benzoyl-2-O-benzyl-α-L-fucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from Sargassum polycystum

  摘要：

  The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed D-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.

  DOI：

  10.1021/jo500503r