The synthesis of some branched-chain-sugar nucleoside analogues

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Abstract
L-(2,3-Epoxy-5–0-trityl-B-n-lyxofuranosyl)urac1l (1) was treated with a number of carbon nucTeophiles. Ethynyl lithium gave S'-deoxy-S'-ethynyl-S'-O-trityi-ara-uridine (2), which was reduced to the corresponding 3'-ethenyl compound (4). Sodium cyanide gave 3'-cyano-3'-deoxy-5'–0-trityl-ara-ur1d1ne (11) which upon alkaline hydrolysis gave the corresponding 3'-carboxamido compound (13). l,3-Dithian-2-yl lithium gave 3'-deoxy-3'-(l,3-d1thian-2-yI)–5'–0-trityl-ara-uridine (14). The trityl group was removed from each of these compounds by mild acidic hydrolysis. Treatment of 2 with 0.1M H2SO4. and mercury (II) acetate afforded 3'-acety1-3'-deoxy-ara-uridine (6) which upon reduction with NaBH4. gave 3'-deoxy-3'-(l-hydroxyethan-l-yl)-ara-urid1ne (7). Acetylation of 6 yielded 5'-0-acetyl–3'-acetyl–2',3'-didehydro-2',3'-dideoxyuridine (8) which upon reduction with NaBH4. produced a mixture of 5'-0-acetyl–2',31-d1dehydro-21,31-d1deoxy-31-(l-hydroxyethan-l-yl)ur1d1ne (9) andl-(R)[5-(S)-acetoxymethyl–4-(l-hydroxyethan-l-yl)-tetrahydrofuran-2-yl]-uraci I (ITT). Reduction of 14 with Raney nickel followed by removal of the trityl group gave 3'-deoxy-3'-methyl-ara-uridine (16).

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