189690-18-4Relevant academic research and scientific papers
Stereoselective Synthesis of Branched and Bicyclo 2′,3′-Dideoxy-threo-furanosyl Nucleosides from Pyranoses Using a Ring Contraction Reaction as the Key Step
Kassou, Mohamed,Castillon, Sergio
, p. 3696 - 3701 (1997)
Bicyclo nucleoside 21 and the branched-chain nucleoside 26 have been stereroselectively synthesized (α:β = 1:4) from a common intermediate 14, which was obtained from methyl 4,6-O-benzylidene-2-deoxy-3-O-triflyl-α-D-arabino-pyranoside (13) through a ring contraction reaction. The branched nucleoside 26 was obtained with an α:β selectivity of 1:4 using either electrophilic selenium or sulfur reagents. In contrast the bicyclo nucleoside 21 was only obtained using the phenylthio derivative 20. The selenium reagents resulted in predominant formation of the α isomer.
