2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-(bromo-difluoro-methyl)-5-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-methoxy-tetrahydro-pyran-4-yl ester | 207342-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-(bromo-difluoro-methyl)-5-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-methoxy-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4R,5R,6R)-5-[bromo(difluoro)methyl]-3,4-bis(2,2-dimethylpropanoyloxy)-6-methoxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 207342-17-4
• 化学式: C₂₃H₃₇BrF₂O₈
• 分子量: 559.443
• InChiKey: RPKZEYIYPSSFAO-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-(bromo-difluoro-methyl)-5-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-methoxy-tetrahydro-pyran-4-yl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以85%的产率得到2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-5-difluoromethyl-4-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-methoxy-tetrahydro-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：

  3,4,6-tri-O-pivaloyl-D-galactal 在 calcium sulfate 、 sodium dithionite 、 碳酸氢钠 、 silver carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 生成 2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-(bromo-difluoro-methyl)-5-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-methoxy-tetrahydro-pyran-4-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

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.