Synthesis of o-L-α-glycerylphosphoryl-L-serine

Abstract

A new efficient method for preparing o-L-α-glycerylphosphoryl-L-serine was presented. D-α, β-isopropylidene glycerol was phosphorylated with phenylphosphoryl dichloride and the resulting o-D-α,β-isopropylidene glycerylphenylphosphoryl chloride was esterified with N-tert-butoxycarbonyl-L-serine ethyl ester in the presence of pyridine to give acetone L-α-glycerylphenylphosphoryl-N-tert-butoxycarbonyl-L-serine ethyl ester. Finally, the protective groups were removed by two-step hydrolysis while strictly controlling pH value. The reaction to produce (1, 2), (5, 6)-diisopropylidene-D-mannitol, which is the key precursor for the preparation of D-α, β-isopropylidene glycerol, was monitored by using gas chromatography-mass spectrometer in order to obtain an optimum yield of 65%. All compounds were characterized through elemental analysis, infrared spectra, ¹H, ¹³C, ³¹P-nuclear magnetic resonance spectra and mass spectra.

Keywords

o-L-α-glycerylphosphoryl-L-serine / N-tert-butoxycarbonyl-L-serine ethyl ester / D-α, β-isopropylidene glycerol

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