Synthesis of 1′-homo-N-nucleosides from hexitols

This paper describes a new route for the synthesis of N-(1'-homo-L-gulitol)nucleosides and amino sugar analogues of N-(1'-homo-L-gulitol)nucleosides by nucleophilic epoxide ring-opening followed by O-heterocyclization of 1,2:5,6-di-anhydro-3,4-di-O-benzyl-D-mannitol and 1,2:5,6-dianhydro-3,4-diazido-D-iditol, respectively. Magnesium perchlorate [Mg(ClO4)(2)] was found to be the best catalyst for the reaction of silylated bases, derived from uracil, thymme and adenine, with these bis(epoxides). ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 2003).