N-Acetyl-D-fucosamine (D-FucNAc) is a rare sugar found in a variety of bacterial glycoconjugates. Chemical synthesis of their repeating units heavily relies on the use of orthogonally protected D-FucNAc-derived building blocks, which are available from diverse precursors. Azidonitration of the title 3,4-di-O-acetyl-D-fucal (3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-D-lyxo-hex-1-enitol) has been routinely used in this laboratory to produce large quantities (>20.0 g) of D-fucosamine and derivatives thereof. Accessing the title compound on a large scale from commercially available d-fucose is prohibitively expensive. We have developed a convenient, six-step procedure to produce this valuable compound in 34%–40% overall yield, starting from commercially available 1,2:3,4-di-O-isopropylidene-D-galactose.
