Organoaluminium induced ring-opening of epoxypyranosides. IV. Synthesis and structure of γ-hydroxy-Isoleucine stereoisomers and their corresponding lactones

Article abstract of DOI:10.1016/S0040-4020(01)86574-1

Two γ-hydroxy-isoleucine stereoisomers 8 (2R, 3R, 4R), and 14 (2S, 3R, 4R) as well as their corresponding γ- lactones 9 and 15 were synthesized using a tandem. Me₃Al induced opening of the epoxide and pyranoside rings of benzyl 2,3-anhydro-4-O-(tert-butyldimethylsilyl)-β-L-ribopyranoside (1). The structure of the lactone hydrochloride 9 was confirmed by an X-ray crystal structure determination.