Facile synthesis of 5′-(N-acyl sulfonamide) derivatized nucleosides

The acylation of several primary sulfonamides with N6-benzoyl-2′,3′-isopropylidene-5′-carboxylic acid-5′-deoxyadenosine (1) is described. Literature methods for the construction of the N-acyl sulfonamide functionality proved ineffective for synthesizing 5′-N-acyl sulfonamide derivatives of 1. The combination of DCC/DMAP provided the mild conditions necessary to effect coupling of the protected nucleoside acid with various primary sulfonamides in good to high yield.