(2R,3R,4S,5R,6R)-5-(((2R,4aR,6S,7S,8S,8aS)-7-(benzoyloxy)-8-((2-methoxy-2-oxo-1-phenylethyl)thio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-6-((benzoyloxy)methyl)-2-methoxytetrahydro-2H-pyran-3,4-diyl dibenzoate | 634901-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-5-(((2R,4aR,6S,7S,8S,8aS)-7-(benzoyloxy)-8-((2-methoxy-2-oxo-1-phenylethyl)thio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-6-((benzoyloxy)methyl)-2-methoxytetrahydro-2H-pyran-3,4-diyl dibenzoate
• CAS: 634901-71-6
• 化学式: C₅₇H₅₂O₁₆S
• 分子量: 1025.1
• InChiKey: YJXWMAJTQOWAGZ-JIHQFRNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  74.0
• 可旋转键数：
  17.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  186.88
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-5-(((2R,4aR,6S,7S,8S,8aS)-7-(benzoyloxy)-8-((2-methoxy-2-oxo-1-phenylethyl)thio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-6-((benzoyloxy)methyl)-2-methoxytetrahydro-2H-pyran-3,4-diyl dibenzoate 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 26.0h， 生成 [(2S,3S,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl]-phenyl-acetic acid
  参考文献：
  名称：

  Synthesis of Lactose-Based S-Linked Sialylmimetics of α(2,3)-Sialosides

  摘要：

  A new approach toward the synthesis of lactose-based S-linked sialylmimetics of alpha(2,3)-linked sialosides is described. These compounds, represented by the general structure 3, were prepared from methyl beta-D-lactoside in 11 steps. It was found that the choice of protecting group was crucial to allow the efficient introduction of sulfur at the 3-position of the galactose ring.

  DOI：

  10.1021/ol035733d
• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-5-(((2R,4aR,6S,7R,8S,8aR)-7-(benzoyloxy)-8-hydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-6-((benzoyloxy)methyl)-2-methoxytetrahydro-2H-pyran-3,4-diyl dibenzoate 在 吡啶 、 potassium nitrite 、 4 A molecular sieve 、 乙酸肼 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 (2R,3R,4S,5R,6R)-5-(((2R,4aR,6S,7S,8S,8aS)-7-(benzoyloxy)-8-((2-methoxy-2-oxo-1-phenylethyl)thio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-6-((benzoyloxy)methyl)-2-methoxytetrahydro-2H-pyran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Synthesis of Lactose-Based S-Linked Sialylmimetics of α(2,3)-Sialosides

  摘要：

  A new approach toward the synthesis of lactose-based S-linked sialylmimetics of alpha(2,3)-linked sialosides is described. These compounds, represented by the general structure 3, were prepared from methyl beta-D-lactoside in 11 steps. It was found that the choice of protecting group was crucial to allow the efficient introduction of sulfur at the 3-position of the galactose ring.

  DOI：

  10.1021/ol035733d