Tetrahedron

Generation of C-1′ radicals through a β-(acyloxy) alkyl rearrangement in modified purine and pyrimidine nucleosides

T Gimisis, G Ialongo, C Chatgilialoglu

Index: Gimisis, Thanasis; Ialongo, Giuseppina; Chatgilialoglu, Chryssostomos Tetrahedron, 1998 , vol. 54, # 3-4 p. 573 - 592

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Citation Number: 32

Abstract

The synthesis of protected 1′, 2′-didehydro-2′-deoxyadenosines has been optimized by incorporating a phosphoranylidene protection of the adenine amino function. These unsaturated adenosines have served as substrates for the electrophilic iodopivaloyloxylation leading to new nucleosides modified at the anomeric position. Reaction of halopivaloates 10, 11 and 12 with tributyltin hydride generates indirectly C-1 ...

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