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‐dianhydro‐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, thymine and adenine, with these bis(epoxides). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)