p-methoxyphenyl 3,4-O-benzyl-2-O-trifluoroethylsulfonato-β-D-glucopyranoside | 763129-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,4-O-benzyl-2-O-trifluoroethylsulfonato-β-D-glucopyranoside
• CAS: 763129-81-3
• 化学式: C₂₉H₃₁F₃O₁₀S
• 分子量: 628.62
• InChiKey: FCXWRZBIOROPRL-RKFAPSRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  118.98
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3,4-O-benzyl-2-O-trifluoroethylsulfonato-β-D-glucopyranoside 在 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 作用下， 以 吡啶 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 1.25h， 生成 6-O-acetyl-3,4-O-benzyl-2-O-trifluoroethylsulfonato-α-D-glucopyranosyl-(1-6)-di-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Trifluoroethylsulfonate protected monosaccharides in glycosylation reactions

  摘要：

  A variety of sulfo-protected monosaccharide donors and acceptors were investigated in glycosylation reactions. Trifluoro-ethylsulfonate (SO3TFE) group was compatible with a wide range of activation conditions commonly used with fluoride, imidate, and sulfide donors. In addition, the influence of a SO3TFE group, at the critical 2-position in glycosyl donor, on the stereoselectivity of the glycosylation reaction was studied. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.131
• 作为产物：
  描述：

  p-methoxypheyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifluoroethylsulfonato-β-D-glucopyranoside 在 硼烷四氢呋喃络合物 、 三氟甲磺酸二丁硼 作用下， 反应 5.0h， 以93%的产率得到p-methoxyphenyl 3,4-O-benzyl-2-O-trifluoroethylsulfonato-β-D-glucopyranoside
  参考文献：
  名称：

  Trifluoroethylsulfonate protected monosaccharides in glycosylation reactions

  摘要：

  A variety of sulfo-protected monosaccharide donors and acceptors were investigated in glycosylation reactions. Trifluoro-ethylsulfonate (SO3TFE) group was compatible with a wide range of activation conditions commonly used with fluoride, imidate, and sulfide donors. In addition, the influence of a SO3TFE group, at the critical 2-position in glycosyl donor, on the stereoselectivity of the glycosylation reaction was studied. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.131