[(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-7-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2-chloroacetate | 634901-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-7-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2-chloroacetate
• CAS: 634901-64-7
• 化学式: C₂₂H₂₉ClO₁₂
• 分子量: 520.918
• InChiKey: GIAMYNOMEUVZLO-ATBTVBTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-7-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2-chloroacetate 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 potassium nitrite 、 4 A molecular sieve 、 乙酸肼 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 2-[(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]-4-hydroxy-pentanoic 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：

  氯乙酰氯 、 (2R,4aR,6S,7R,8R,8aR)-6-((2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 在 二正丁基氧化锡 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.5h， 以89%的产率得到[(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-7-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2-chloroacetate
  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

文献信息

• Synthesis of Lactose-Based <i>S</i>-Linked Sialylmimetics of α(2,3)-Sialosides
  作者：Angela Liakatos、Milton J. Kiefel、Mark von Itzstein

  DOI：10.1021/ol035733d

  日期：2003.11.1

  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.