Synthesis of 1′‐Homo‐N‐nucleosides from Hexitols

Abstract

Abstract 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‐dianhydro‐3,4‐di‐ O ‐benzyl‐ D ‐mannitol and 1,2:5,6‐dianhydro‐3,4‐diazido‐ D ‐iditol, respectively. Magnesium perchlorate [Mg(ClO 4 ) 2 ] was found to be the best catalyst for the reaction of silylated bases, derived from uracil, thymine and adenine, with these bis(epoxides). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)