Stereoselective Reformatskii-Claisen rearrangement: synthesis of 2',3'-dideoxy-6',6'-difluoro-2'-thionucleosides.
A new approach for the stereoselective synthesis of 2',3'-dideoxy-6',6'-difluoro-2'-thionucleosides, analogues of highly bioactive L-OddC and 3TC, has been developed via TMSCl/pyridine induced stereoselective Reformatskii-Claisen rearrangement of secondary allyl chlorodifluoroacetate and then a regioselective Pummerer reaction to introduce bases.
Zheng
Feng
F
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China.
Zhang
Xingang
X
Qing
Feng-Ling
FL
D018360:Crystallography, X-Ray; D005461:Fluorine / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry; D013237:Stereoisomerism; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
D009705:Nucleosides; D013872:Thionucleosides; D005461:Fluorine