Synthesis ofo-L-α-glycerylphosphoryl-L-serine

来源期刊：中南大学学报(英文版)2005年第6期

论文作者：唐瑞仁 严子耳 罗一鸣

文章页码：693 - 698

Key words：o-L-α-glycerylphosphoryl-L-serine;N-tert-butoxycarbonyl-L-serine ethyl ester;D-α,β-isopropylidene glycerol

Abstract: A new efficient method for preparingo-L-α-glycerylphosphoryl-L-serine was presented.D-α,β-isopropylidene glycerol was phosphorylated with phenylphosphoryl dichloride and the resultingo-D-α,β-isopropylidene glycerylphenylphosphoryl chloride was esterified withN-tert-butoxycarbonyl-L-serine ethyl ester in the presence of pyridine to give acetoneL-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 ofD-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.