p-Tolyl 4-O-acetyl-3,6-di-O-benzyl-2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside | 1607433-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-Tolyl 4-O-acetyl-3,6-di-O-benzyl-2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-5-[(4-methoxyphenyl)methoxy]-6-(4-methylphenyl)sulfanyl-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 1607433-77-1
• 化学式: C₃₇H₄₀O₇S
• 分子量: 628.786
• InChiKey: DVNMFYCGWUXQLN-AESTUDHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  97.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-Methoxyphenyl 4-O-benzoyl-2-O-benzyl-α-L-fucopyranoside 、 p-Tolyl 4-O-acetyl-3,6-di-O-benzyl-2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 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， 以79%的产率得到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
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 四丁基硫酸氢铵 、 对甲苯磺酸 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 71.0h， 生成 p-Tolyl 4-O-acetyl-3,6-di-O-benzyl-2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside
  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