D. Horton, J. S. Jewell, E. K. Just
May 1, 1971
Citations
0
Influential Citations
25
Citations
Journal
Carbohydrate Research
Abstract
Abstract Treatment of 1,6-anhydro-2,3- O -isopropylidene-β- D - lyxo -hexopyranos-4-ulose ( 1 ) with sodium deuteroxide in deuterium oxide leads to regiospecific and stereo-specific incorporation of deuterium at C-3, to give the 3- C -deuterated analog ( 2 ) of the ketone 1 . Reduction of 1 with sodium borohydride gives 1,6-anhydro-2,3- O -isopropylidene-β- D -talopyranose ( 3 ) stereospecifically, and the 4- C -deuterated analog ( 4 ) was obtained when the reduction was effected with sodium borodeuteride. Similar reductions of the deuterated ketone 2 gave the 3- C -deuterated analog ( 5 ) of 3 and the 3,4-di- C -deuterated analog ( 6 ) of 3 , respectively. The 100-MHz n.m.r. spectrum of 3 was interpreted completely by comparison of its spectrum with those of the deuterated analogs 4-6 . Alterations in the appearance (but not the field position) of various signals in the n.m.r. spectrum of 3 as a function of isotopic substitution permitted complete, reliable determination of chemical shifts and coupling constants for all protons in the molecule.