ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside | 515813-86-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside
• CAS: 515813-86-2
• 化学式: C₂₁H₂₆O₉S
• 分子量: 454.498
• InChiKey: WOIRKPZNKDPVJJ-XLIFZOOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-(三甲硅基)乙醇 、 ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以73%的产率得到2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  SYNTHESIS OF 2-(TRIMETHYLSILYL)ETHYL α-d-MANNOPYRANOSIDES REVISITED

  摘要：

  Glycosylation of 2-(trimethylsilyl)ethanol with various ethyl 1-thioglycosides, which were activated with N-iodosuccinimide and silver triflate, was studied. The starting thioglycosides, some prepared for the first time, were obtained conventionally from the corresponding alpha-1-acetates. When beta-1-acetates were more readily available, these were converted to the alpha-anomers by anomerization, prior to the glycosylation. Using ethyl 1-thioglycosides as glycosyl donors, especially those bearing a pivaloyl or a nonparticipating group at O-2, the corresponding 2-(trimethylsilyl)ethyl alpha-D-mannopyranosides were obtained in excellent yields.

  DOI：

  10.1081/car-120016846
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-O-benzoyl-β-D-mannopyranose 在 硫酸 、 三氟化硼乙醚 、 乙酸酐 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  SYNTHESIS OF 2-(TRIMETHYLSILYL)ETHYL α-d-MANNOPYRANOSIDES REVISITED

  摘要：

  Glycosylation of 2-(trimethylsilyl)ethanol with various ethyl 1-thioglycosides, which were activated with N-iodosuccinimide and silver triflate, was studied. The starting thioglycosides, some prepared for the first time, were obtained conventionally from the corresponding alpha-1-acetates. When beta-1-acetates were more readily available, these were converted to the alpha-anomers by anomerization, prior to the glycosylation. Using ethyl 1-thioglycosides as glycosyl donors, especially those bearing a pivaloyl or a nonparticipating group at O-2, the corresponding 2-(trimethylsilyl)ethyl alpha-D-mannopyranosides were obtained in excellent yields.

  DOI：

  10.1081/car-120016846