4-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroethoxysulfoxyamino-β-D-glucopyranoside | 1185733-84-9

• 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: 4-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroethoxysulfoxyamino-β-D-glucopyranoside
• 英文别名: 2,2,2-trichloroethyl 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]sulfamate
• CAS: 1185733-84-9
• 化学式: C₂₉H₃₀Cl₃NO₇S₂
• 分子量: 675.051
• InChiKey: BFABVDWHLBZBSZ-PYFBZWTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroethoxysulfoxyamino-β-D-glucopyranoside 在 甲酸铵 、 锌 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以84%的产率得到4-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-2-sulfoxyamino-β-D-glucopyranoside ammonium salt
  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-tolyl 2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 、 2,2,2-trichloroethoxysulfuryl-1,2-dimethylimidazole triflate 在 1,2-二甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到4-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroethoxysulfoxyamino-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.