Abstract
Synthesis of sugar phosphate derivatives by means of phosphite triester method is described. Seven glucose phosphotriester derivatives have been prepared, i.e. dimethyl, methyl n-propyl, and methyl isopropyl (1, 2:5, 6-di-O-isopropylidene-α-D-glucofuranose-3-) phosphate (5, 7 and 8); methyl bis-(1, 2:5, 6-di-O-isopropylidene-α-D-glucofuranose-3-) phosphate (6); methyl bis-(1, 2, 3, 4-tetra-O-acetyl-β-D-glucopyranose-6-) phosphate (9); methyl bis-(1, 2-O-isopropylidene-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 alcohols showed that methanol, n-propanol, isopropanol and as well as the glucose derivatives reacted normally 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 easily achieved by the action of t-butyl amine and thus, t-butyl ammonium bis-(1, 2:5, 6-di-O-isopropylidene-α-D-glucofuranose-3-) phosphate t-butyl amine salt (12) has been obtained from its parent phosphotriester in nearly quantitative yield. The mass spectra data of di-O-isopropylideneglucose phosphate reveals that the cleavage of these compounds follows a general pattern and can be used for their characterization.
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