REACTION OF METHYL DIAZOACETATE WITH 2,3 O-ISOPROPYLIDENE-D-GLYCERALDEHYDE. STEREOSELECTIVITY IN THE SYNTHESIS OF 2-DEOXY-D-ALDONATES AND 2-DEOXY-γ,D-ALDONOLACTONES.

Article abstract of DOI:10.1016/S0040-4020(01)87898-4

The reaction of 2,3-O-isopropylidene-D-glyceraldehyde with diazoacetates are revised.In the absence of catalyst, the methyl (3S,4R) and (3R,4R)-4,5-O-isopropylidene-2-diazo-3,4,5-trihydroxypentanoate (4a and 4b) were the new and main products in a high stereoselective reaction (84:16).These products were easily converted into the corresponding 2-deoxy-3-ulosonates (3), 2-deoxy-aldonates (6,7 and 8) and 2-deoxy-γ,D-aldonolactones (9 and 10).