Fuente Cebrián, Àlex de laVerdaguer i Espaulella, XavierRiera i Escalé, Antoni2018-01-262018-12-212017-12-211434-193Xhttps://hdl.handle.net/2445/119330A stereoselective synthesis of 2-acetamido-1,2-dideoxyaltronojirimycin (8) and its manno epimer 9 is described. The synthetic approach is based on key bicyclic carbamate 7, which is easily accessible with high enantiomeric purity on a multigram scale by Sharpless asym. epoxidn. of 1,4-pentadien-3-ol or 2,4-pentadien-1-ol. This procedure completes an efficient stereodivergent approach to five isomers of 2-acetamido-1,2-dideoxyiminosugars in high overall yields starting from the same key intermediate 7. The approach described in this paper is based on control of the stereoselectivity of the sulfite ring-opening reaction to give retention of configuration through anchimeric assistance from the endocyclic amine.7 p.application/pdfeng(c) Wiley-VCH, 2017Disseny de medicamentsInhibidors enzimàticsDrug designEnzyme inhibitorsinfo:eu-repo/semantics/article6756352018-01-26info:eu-repo/semantics/openAccess