Synthesis of (+)- and (-)-nojirimycin and their 1-deoxy derivatives from myo-inositol

Article abstract of DOI:10.1016/S0008-6215(92)84242-K

The conversion of the naturally abundant cyclitol, myo-inositol (4), into (+)-nojirimycin (1a), its enantiomer (1b), and their 1-deoxy analogues (2a and 2b) is described. Biological assay of 2a, 2b, and the bisulfite adducts of 1a and 1b (3a and 3b) showed that the compounds having the unnatural L-gluco configuration (2b and 3b) possess moderate-to-high inhibitory activity against almond β-D-glucosidase and bovine liver β-D-galactosidase.