Link to DOI – 10.1055/s-0035-1561323
Synthesis, 2016, 48, 1177-1180
A novel gram-scale synthesis of 1-deoxymannojirimycin from tetra-O-benzyl-d-glucopyranose in 9 steps and 28% overall yield with a limited number of purification steps is reported. The synthetic strategy is based on the regioselective deprotection and subsequent inversion of configuration of the OH group at C-2 in tetra-O-benzyl-d-glucono-δ-lactam, also an advanced intermediate toward the synthesis of 1-deoxynojirimycin derivatives.