Synthesis of L- and D-beta-3'-Deoxy-3',3'-difluoronucleosides.
Both L- and D-beta-3'-deoxy-3',3'-difluoronucleosides were synthesized starting from the key intermediate difluorohomoallyl alcohol 11. Deoxo-Fluor was accidentally found to be efficient in reversing the hydroxyl configuration of 34, and the desired product 41 was provided in good yield.
Xu
Xiu-Hua
XH
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 354 Fenglin Lu, Shanghai 200032, China.
Qiu
Xiao-Long
XL
Zhang
Xingang
X
Qing
Feng-Ling
FL
D000438:Alcohols / Q000737:chemistry*; D005466:Fluorocarbons / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; C516100:D-beta-3'-Deoxy-3',3'-difluoronucleoside; D005466:Fluorocarbons; D009705:Nucleosides