A Chemo-Enzymatic Synthesis of D-Allosamine Derivatives from Tri-O-acetyl- D-glucal

Article abstract of DOI:10.1246/bcsj.70.2535

N-Acetyl-D-allosamine and its derivatives were synthesized from tri-O-acetyl-D-glucal based on lipase-catalyzed selective protection of primary alcohols, [3,3] sigmatropic rearrangement of allylic trichloroacetimidates, and stereo- selective ruthenium-catalyzed dihydroxylation. In the course of this study, it was revealed that the Pseudomonas lipase- catalyzed acetylation occurred in a high yield (> 90%) exclusively at the primary alcohols of three Ferrier rearrangement products derived from tri-O-acetyl-D-glucal.