Regioselective halogenation of some 2,3-anhydro pyrimidine nucleosides with dilithium tetrahalocuprates.
The reaction of 1-(2,3-anhydro-5-O-trityl-beta-D-lyxofuranosyl)-2-O-methyluracil (1a) and its thymine analogue (1b) with dilithium tetrahalocuprate (Li2CuX4) revealed excellent to perfect regioselectivity, yielding 2,2'-anhydro-3'-halonucleosides (2a-d), while the same reactions with 2,3-anhydro uracil and thymine nucleosides (4a,b) gave arabinosyl (5a-d) and xylosyl halohydrins (6a-d) with the respective product ratio of 7:3 to 8:2. compounds 5 and 6 were isolated as the 2-O-(7) and 3- O-mesyl derivatives (8).
Minamoto
K
K
Department of Applied Chemistry, School of Engineering, Nagoya University, Japan.
Watanabe
K
K
Yanagihara
K
K
D001965:Bromides / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D011741:Pyrimidine Nucleosides / Q000737:chemistry*
D001965:Bromides; D002712:Chlorides; D011741:Pyrimidine Nucleosides; C079759:dilithium tetrachlorocuprate; C079760:dilithium tetrabromocuprate; D003300:Copper