6-Deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, D-fuco-nojirimycin and their 1-deoxyderivatives via hetero-Diels-Alder cycloadditions

Article abstract of DOI:10.1016/S0040-4020(97)00898-3

Nucleophilic ring opening of the cyclic sulfates (±)-9c and D-9c and of the epoxide (±)-13, or double substitution of the bis-triflate D-10 (derived from the Diels-Alder adduct of hexodienal dimethylacetal to achiral or enantiomerically pure nitroso-derivatives) led to 6-deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, to D-fuco-nojirimycin and to their 1-deoxyderivatives via their crystalline 1-deoxy-1-sulfonic acid derivatives (sulfite adducts). 6-Deoxy-nojirimycin and its isomers are mixtures of α- and β-anomers and of the corresponding imine.