Synthesis of 5-deazaflavin adenine dinucleotide (5-dFAD) using a modified triester approach

Starting from D-ribose and 3,4-xylidine, a fifteen-step synthesis is described for the preparation of 5-dFAD (18). The synthesis involves as key intermediates, 5-deazariboflavin (8), its 2′,3′,4′-tris-O-(tetrahydropyranyl) derivative (12) and 2′,3′,4′-tris-O-(tetrahydropyranyl)-5′-O-(morpholinophosphonyl)-5-deazariboflavin (15).