p-tolyl 3,6-di-O-benzyl-2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside | 1607433-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 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-ol
• CAS: 1607433-75-9
• 化学式: C₃₅H₃₈O₆S
• 分子量: 586.749
• InChiKey: BJIHGPYPZFLSJV-NVCPMKERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-tolyl 3,6-di-O-benzyl-2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 在 4-二甲氨基吡啶 、 三乙胺 、 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 8.5h， 生成 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：

  在 四丁基硫酸氢铵 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 66.0h， 生成 p-tolyl 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