3,4-di-O-benzoyl-6-O-[(tert-butyl)dimethylsilyl]-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride | 304453-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3,4-di-O-benzoyl-6-O-[(tert-butyl)dimethylsilyl]-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride
• CAS: 304453-32-5
• 化学式: C₃₄H₃₄Cl₂FNO₈Si
• 分子量: 702.636
• InChiKey: YAUMSNNETTZFET-HWVUQVAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  47.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  108.44
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzoyl-6-O-[(tert-butyl)dimethylsilyl]-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride 在 calcium sulfate 、 TrB(C₆F₅)4 、 氢氟酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 21.67h， 生成 3,4-di-O-benzoyl-6-O-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  A Catalytic and Stereoselective Glycosylation withβ-Glycosyl Fluorides

  摘要：

  A catalytic and stereoselective glycosylation of several glycosyl accepters with beta-D-glycosyl fluoride was successfully performed in the presence of a catalytic amount of trityl tetrakis(pentafluorophenyl)borate (TrB(C6F5)(4)) or trifluoromethanesulfonic acid (TfOH). When TrB(C6F5)(4) was used as a catalyst in the solvent pivalonitrile/(trifluoromethyl)benzene 1:5, the glycosylation proceeded smoothly to afford the glycosides in high yields with high beta-D-stereoselectivities (see Table 3). Further, the glycosylation by the armed-disarmed strategy in the presence of this catalyst was established (see Table 4). Similarly, glycosylation catalyzed by the strong protic acid TfOH afforded the corresponding beta-D-glycosides in good-to-excellent yields on treating beta-D-glycosyl fluorides having a 2-O-benzoyl group with various glycosyl accepters including thioglycosides (see Tables 6 and 7).

  DOI：

  10.1002/1522-2675(20000809)83:8<1901::aid-hlca1901>3.0.co;2-q
• 作为产物：
  描述：

  dodecyl 3,4-di-O-benzoyl-6-O-[(tert-butyl)dimethylsilyl]-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以92%的产率得到3,4-di-O-benzoyl-6-O-[(tert-butyl)dimethylsilyl]-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  A Catalytic and Stereoselective Glycosylation withβ-Glycosyl Fluorides

  摘要：

  A catalytic and stereoselective glycosylation of several glycosyl accepters with beta-D-glycosyl fluoride was successfully performed in the presence of a catalytic amount of trityl tetrakis(pentafluorophenyl)borate (TrB(C6F5)(4)) or trifluoromethanesulfonic acid (TfOH). When TrB(C6F5)(4) was used as a catalyst in the solvent pivalonitrile/(trifluoromethyl)benzene 1:5, the glycosylation proceeded smoothly to afford the glycosides in high yields with high beta-D-stereoselectivities (see Table 3). Further, the glycosylation by the armed-disarmed strategy in the presence of this catalyst was established (see Table 4). Similarly, glycosylation catalyzed by the strong protic acid TfOH afforded the corresponding beta-D-glycosides in good-to-excellent yields on treating beta-D-glycosyl fluorides having a 2-O-benzoyl group with various glycosyl accepters including thioglycosides (see Tables 6 and 7).

  DOI：

  10.1002/1522-2675(20000809)83:8<1901::aid-hlca1901>3.0.co;2-q