Convenient Synthesis of 2‐Azido‐2‐deoxy‐aldoses by Diazo Transfer

Abstract

Abstract Diazo transfer from trifluoromethanesulfonyl azide (TfN 3 ) to 2‐amino‐2‐deoxy‐glycoses constitutes a high‐yielding, simple procedure for the preparation of partially protected or unprotected 2‐azido‐2‐deoxy‐aldoses. Thus, the D ‐allosamine derivative 2 gave 93% of 3 , while diazo transfer to D ‐glucosamine, D ‐mannosamine, and D ‐galactosamine, followed by acetylation, yielded the azides 5 , 7 , and 9 in yields of 74–91, 65, and 70%, respectively.