(2R,4aR,6S,7R,8R,8aS)-N-[[(2R,4aR,6S,7R,8R,8aS)-6-(4-methylphenyl)sulfanyl-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]sulfamoyl]-6-(4-methylphenyl)sulfanyl-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-amine | 1185733-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (2R,4aR,6S,7R,8R,8aS)-N-[[(2R,4aR,6S,7R,8R,8aS)-6-(4-methylphenyl)sulfanyl-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]sulfamoyl]-6-(4-methylphenyl)sulfanyl-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-amine
• CAS: 1185733-87-2
• 化学式: C₅₄H₅₆N₂O₁₀S₃
• 分子量: 989.244
• InChiKey: WCRYBANXBTVQGY-LUZVVHJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  69
• 可旋转键数：
  16
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  191
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  p-tolyl 2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 2,2,2-三氯乙基氯磺酸酯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以70%的产率得到(2R,4aR,6S,7R,8R,8aS)-N-[[(2R,4aR,6S,7R,8R,8aS)-6-(4-methylphenyl)sulfanyl-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]sulfamoyl]-6-(4-methylphenyl)sulfanyl-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-amine
  参考文献：
  名称：

  O- and N-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts

  摘要：

  A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl-protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS 9) proved to be a superior sulfating compared to SISs bearing no alkyl groups or bulkier alkyl groups on the imidazolium ring. Difficult O-sulfations that required prolonged reaction times and a large excess of the SIS bearing a 1-methylimidazolium group (SIS 5) were achieved in high yield using less than half the amount of SIS 9 in less time. Certain N-sulfated compounds that were practically inaccessible using SIS 5 were obtained in excellent yield using SIS 9.

  DOI：

  10.1021/jo9014112