p-methoxyphenyl 2,3-di-O-acetyl-6-O-benzyl-β-D-glucopyranoside | 1009006-57-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3-di-O-acetyl-6-O-benzyl-β-D-glucopyranoside
• CAS: 1009006-57-8
• 化学式: C₂₄H₂₈O₉
• 分子量: 460.481
• InChiKey: IIXKYQKIRNYBIA-GNADVCDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3-di-O-acetyl-6-O-benzyl-β-D-glucopyranoside 、 1-(2,2,2-trichloroethoxysulfuryl)-2-ethyl-3-methylimidazolium triflate 在 1,2-二甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以68%的产率得到p-methoxyphenyl 2,3-di-O-acetyl-4-O-trichloroethylsulfo-6-O-benzyl-β-D-glucopyranoside
  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
• 作为产物：
  描述：

  p-methoxyphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到p-methoxyphenyl 2,3-di-O-acetyl-6-O-benzyl-β-D-glucopyranoside
  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