methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-imino-N-(trichloroethoxysulfonyl)-β-D-glucopyranoside | 1185733-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 英文名称: methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-imino-N-(trichloroethoxysulfonyl)-β-D-glucopyranoside
• 英文别名: 2,2,2-trichloroethyl (1S,2S,4R,5R,7R,10R)-5-methoxy-10-phenyl-6,9,11-trioxa-3-azatricyclo[5.4.0.02,4]undecane-3-sulfonate
• CAS: 1185733-95-2
• 化学式: C₁₆H₁₈Cl₃NO₇S
• 分子量: 474.746
• InChiKey: GQPNFGNCSXIPGZ-VGXCDAHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  91.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,2,2-trichloroethoxysulfuryl-1,2-dimethylimidazole triflate 、 methyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 1,2-二甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-imino-N-(trichloroethoxysulfonyl)-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

文献信息

• <i>O</i>- and <i>N</i>-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts
  作者：Laura J. Ingram、Ahmed Desoky、Ahmed M. Ali、Scott D. Taylor

  DOI：10.1021/jo9014112

  日期：2009.9.4

  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.