[(2R,3R,4R,5R,6R)-6-bromo-5-[bromo(difluoro)methyl]-3,4-bis(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate | 207342-16-3

• 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: [(2R,3R,4R,5R,6R)-6-bromo-5-[bromo(difluoro)methyl]-3,4-bis(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 207342-16-3
• 化学式: C₂₂H₃₄Br₂F₂O₇
• 分子量: 608.313
• InChiKey: KCIJWYVDLAZUIC-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R,6R)-6-bromo-5-[bromo(difluoro)methyl]-3,4-bis(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate 在 calcium sulfate 、 四丁基氟化铵 、 silver carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 2,2-Dimethyl-propionic acid (2R,3R,6R)-2-(2,2-dimethyl-propionyloxymethyl)-6-methoxy-5-trifluoromethyl-3,6-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  A New Method for the Selective Introduction of Difluoromethyl and Trifluoromethyl Groups into Sugar Moieties

  摘要：

  We have studied the fluoroalkylation of the glucal 1 and the galactal 4 with dibromodifluoromethane via the 2-C-bromodifluoromethyl-substituted glycosyl bromides 2 and 5, respectively, followed by glycosylation to the methyl beta-D-glycosides 3 and 6. The bromodifluoromethyl groups in the 2 position of the compounds 3 and 6 were converted into difluoromethyl and trifluoromethyl groups, respectively, giving the fluorinated monosaccharides 7-10.

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<919::aid-ejoc919>3.0.co;2-3
• 作为产物：
  描述：

  二溴二氟甲烷 、 3,4,6-tri-O-pivaloyl-D-galactal 在 sodium dithionite 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 生成 [(2R,3R,4R,5R,6R)-6-bromo-5-[bromo(difluoro)methyl]-3,4-bis(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  A New Method for the Selective Introduction of Difluoromethyl and Trifluoromethyl Groups into Sugar Moieties

  摘要：

  We have studied the fluoroalkylation of the glucal 1 and the galactal 4 with dibromodifluoromethane via the 2-C-bromodifluoromethyl-substituted glycosyl bromides 2 and 5, respectively, followed by glycosylation to the methyl beta-D-glycosides 3 and 6. The bromodifluoromethyl groups in the 2 position of the compounds 3 and 6 were converted into difluoromethyl and trifluoromethyl groups, respectively, giving the fluorinated monosaccharides 7-10.

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<919::aid-ejoc919>3.0.co;2-3

文献信息

• A New Method for the Selective Introduction of Difluoromethyl and Trifluoromethyl Groups into Sugar Moieties
  作者：Ralf Miethchen、Martin Hein、Helmut Reinke

  DOI：10.1002/(sici)1099-0690(199805)1998:5<919::aid-ejoc919>3.0.co;2-3

  日期：1998.5

  We have studied the fluoroalkylation of the glucal 1 and the galactal 4 with dibromodifluoromethane via the 2-C-bromodifluoromethyl-substituted glycosyl bromides 2 and 5, respectively, followed by glycosylation to the methyl beta-D-glycosides 3 and 6. The bromodifluoromethyl groups in the 2 position of the compounds 3 and 6 were converted into difluoromethyl and trifluoromethyl groups, respectively, giving the fluorinated monosaccharides 7-10.