A concise synthesis of 4,6-dideoxy-4-base-6-amino-2,5-anhydro-l-mannitols

Abstract: 3,6-Di-O-methanesulfonyl-2,5-anhydro-l-idofuranose dimethyl acetal 9 was reacted with NaN3 in DMF to give 6-azido substituted carbohydrate 10 selectively. A series of 6-amino-isonucleosides 4a–d were synthesized by the reaction of nucleobases with epoxide 13, followed by hydrolysis, reduction, and deprotection, in good yield. [Copyright &y& Elsevier]