Synthesis of glucose phosphate derivatives by the phosphite triester method

Synthesis of sugar phosphate derivatives by means of phosphite triester method is de-scribed.Seven glucose phosphotriester derivatives have been prepared,i.e.dimethyl,methyl n-pro-pyl,and methyl isopropyl(1,2:5,6-di-O-isopropylidene-α-D-glucofuranose-3-)phosphate(5,7and 8);methyl bis-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranose-3-)phosphate(6);methylbis-(1,2,3,4-tetra-O-acetyl-β-D-glucopyranose-6-)phosphate(9);methyl bis-(1,2-O-isopropyl-idene-3,5-O-benzylidene-α-D-glucofuranose-6-)phosphate(10);and methyl(1,2,5,6-di-O-iso-propylidene-α-D-glucofuranose-3-)(1,2,3,4-tetra-O-acetyl-β-D-glucopyranose-6-)phosphate(11).The results of the displacement of second chlorine atom of the reagent by different alcoholsshowed that methanol,n-propanol,isopropanol and as well as the glucose derivatives reacted nor-mally to give the expected phosphite esters which yield the expected phosphate products after oxidation,but not the t-butanol.Removal of methyl group from a phosphotriester linkage can be easilyachieved by the action of t-butyl amine and thus,t-butyl ammonium bis-(1,2:5,6-di-O-isopropyl-idene-α-D-glucofuranose-3-)phosphate t-butyl amine salt(12)has been obtained from its parentphosphotriester in nearly quantitative yield.The mass spectra data of di-O-isopropylideneglucose phosphate reveals that the cleavage ofthese compounds follows a general pattern and can be used for their characterization.