3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride | 304453-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride
• 英文别名: [(2R,3S,4R,5R,6S)-4-acetyloxy-5-(5,6-dichloro-1,3-dioxoisoindol-2-yl)-6-fluoro-3-hydroxyoxan-2-yl]methyl acetate
• CAS: 304453-44-9
• 化学式: C₁₈H₁₆Cl₂FNO₈
• 分子量: 464.231
• InChiKey: DVEAKACKCJVDQC-OXGONZEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四-O-苄基-β-D-吡喃葡萄糖酰氟 、 3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride 在 calcium sulfate 、 TrB(C₆F₅)4 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranosyl fluoride 、 3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-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：

  在 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三甲基氯硅烷 、 二乙胺基三氟化硫 、 3 A molecular sieve 、 sodium cyanoborohydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 34.0h， 生成 3,6-di-O-acetyl-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