Synthesis of base-modified dihydropacidamycins

We describe in this paper the synthesis of 1,2-di-O-acetyl-5-azido-3,5-dideoxy-α,β- -arabinofuranose, a carbohydrate donor that was used for the synthesis of 1-(5′-amino-3′,5′-dideoxy-α- -arabinofuranosyl)uracil, the nucleoside found in dihydropacidamycin D. The carbohydrate donor was also used for the synthesis of a set of new nucleosides that were introduced in new dihydropacidamycins. These compounds were tested for biological activity, and the results showed that uracil is the only base recognized by MraY.