6-O-tert-butyldiphenylsilyl-2-O-benzoyl-α-D-mannopyranosyl fluoride | 1187620-65-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-O-tert-butyldiphenylsilyl-2-O-benzoyl-α-D-mannopyranosyl fluoride
• 英文别名: Bz(-2)[TBDPS(-6)]a-Man1F；[(2R,3S,4S,5S,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-fluoro-4,5-dihydroxyoxan-3-yl] benzoate
• CAS: 1187620-65-0
• 化学式: C₂₉H₃₃FO₆Si
• 分子量: 524.661
• InChiKey: WJEVQLHGZBRLOF-VKINHPFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 在 氟化氢吡啶 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到6-O-tert-butyldiphenylsilyl-2-O-benzoyl-α-D-mannopyranosyl fluoride
  参考文献：
  名称：

  Reaction of 1,2-Orthoesters with HF−Pyridine: A Method for the Preparation of Partly Unprotected Glycosyl Fluorides and Their Use in Saccharide Synthesis

  摘要：

  Glycosyl fluorides can be prepared In an efficient manner by treatment of pyranose- or furanose-derived 1,2-orthoesters, with hydrogen fluoride pyridine (HF-py). The method is compatible with the presence of a variety of protecting groups, including tert-butyldiphenyl silyl ethers, and can be applied to sugar derivatives with free hydroxyl groups, thus avoiding the need for the protection-deprotection steps.

  DOI：

  10.1021/ol901630d

文献信息

• Reaction of 1,2-Orthoesters with HF−Pyridine: A Method for the Preparation of Partly Unprotected Glycosyl Fluorides and Their Use in Saccharide Synthesis
  作者：J. Cristóbal López、Juan Ventura、Clara Uriel、Ana M. Gómez、Bert Fraser-Reid

  DOI：10.1021/ol901630d

  日期：2009.9.17

  Glycosyl fluorides can be prepared In an efficient manner by treatment of pyranose- or furanose-derived 1,2-orthoesters, with hydrogen fluoride pyridine (HF-py). The method is compatible with the presence of a variety of protecting groups, including tert-butyldiphenyl silyl ethers, and can be applied to sugar derivatives with free hydroxyl groups, thus avoiding the need for the protection-deprotection steps.