[(2R,3R,4S,5R,6R)-3-[[(2R,4aR,6S,7S,8S,8aS)-8-acetylsulfanyl-7-benzoyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-4,5-dibenzoyloxy-6-methoxyoxan-2-yl]methyl benzoate | 634901-66-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3R,4S,5R,6R)-3-[[(2R,4aR,6S,7S,8S,8aS)-8-acetylsulfanyl-7-benzoyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-4,5-dibenzoyloxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 634901-66-9
• 化学式: C₅₀H₄₆O₁₅S
• 分子量: 918.972
• InChiKey: LESJKPSSGYIIBH-PHQOTWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  66
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  203
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3-[[(2R,4aR,6S,7S,8S,8aS)-8-acetylsulfanyl-7-benzoyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-4,5-dibenzoyloxy-6-methoxyoxan-2-yl]methyl benzoate 在 4 A molecular sieve 、 乙酸肼 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 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
• 作为产物：
  描述：

  三氟甲磺酸苄酯 在 吡啶 、 4-二甲氨基吡啶 、 potassium nitrite 、 乙酸肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 [(2R,3R,4S,5R,6R)-3-[[(2R,4aR,6S,7S,8S,8aS)-8-acetylsulfanyl-7-benzoyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-4,5-dibenzoyloxy-6-methoxyoxan-2-yl]methyl benzoate
  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