327601-80-9Relevant articles and documents
Synthesis of 4-octuloses. Part 7: Highly stereoselective synthesis of 2,3-anhydrosugar derivatives as key intermediates in the preparation of sugar β-lactams
Izquierdo, Isidoro,Plaza, Maria T.,Robles, Rafael,Mota, Antonio J.
, p. 4509 - 4519 (2000)
Reaction of either 1 or 4 with (N,N-dibenzylcarbamoylmethylene)dimethylsulfurane 2 in DMSO afforded 2,3-anhydro-4,5-O-isopropylidene-D-arabino-pentonamide 3 or N,N-dibenzyl 2,3-anhydro-4,5:6,7-di-O-isopropylidene-β-D-glycero-D-galacto-oct-4-u lo-4,8-pyranosonamide 5, respectively. The configurations of 3 and 5 were determined on the basis of their spectroscopic data, in the first case, and by chemical transformation into the known 2,3-anhydro-4,5:6,7-di-O-isopropylidene-β-D-glycero-D-galacto-oct-4-u lo-4,8-pyranose 11. Treatment of 3 and 5 with lithium hexamethyldisilazide in THF provided the corresponding sugar β-lactams 12, 13 and 14, respectively.