Tetrahedron

Synthesis of 3'-c-cyano-3'-deoxy-pentofuranosylthymine nucleosides

A Calvo-Mateo, MJ Camarasa, A Díaz-Ortíz, G Federico…

Index: Calvo-Mateo; Camarasa; Diaz-Ortiz; De Las Heras; Alemany Tetrahedron, 1988 , vol. 44, # 15 p. 4895 - 4903

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Citation Number: 24

Abstract

A series of 3'-C-cyano-3'-deoxy-pentafuranosylthymlne nucleosides have been synthesized from 1-(β-D-ribofuranosyl) thyBlne (7). 2', 5'-Selective protection of 7 followed by oxidation afforded the corresponding 3'-ketonucleoside (9). The latter reacted with NaCN to give a mixture of 3'-cyanohydrins which were 3'-deoxygenated to afford 1-2', 5'-di-O-(t- butyldimethylsilyl)-3'-C-eyario-3'-deoxy-β-DXXX-xylo-pentofuranosyl thylne (14). ...