Synthesis of 2‑Nitroglycals from Glycals Using the Tetrabutylammonium Nitrate–Trifluoroacetic Anhydride–Triethylamine Reagent System and Base-Catalyzed Ferrier Rearrangement of Acetylated 2‑Nitroglycals

A reagent
system comprising tetrabutylammonium nitrate–trifluoroacetic
anhydride–triethylamine has been developed for the synthesis
of 2-nitroglycals from various protected glycals. The base-catalyzed
Ferrier rearrangement on tri-O-acetylated 2-nitroglycals
has been reported for the first time. Reactivity of these nitroacetates
and associated selectivity has been examined, and some of the products
have been converted into 2,3-diamino-2,3-dideoxyglycosides and methyl N-acetyl-d-lividosaminide.