O. O. Kolodyazhnaya, A. O. Kolodyazhnaya, O. I. Kolodyazhnyĭ
May 23, 2013
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Journal
Russian Journal of General Chemistry
Abstract
A scheme for the synthesis of phosphonic analog of glutamic acid starting from tert-butyl N-tert-butoxycarbonylaspartate I was developed. The latter was obtained from aspartic acid by the previously described method [1, 2]. The carboxy group of compound I was acylated with ethyl chloroformate and reduced with sodium borohydride in methanol to give tertbutyl-(S)-N-(tert-butoxycarbonyl)homoserine (S)-II [2]. The latter was converted to the bromide (S)-III via the reaction with triphenylphosphine and bromotrichloromethane [3]. Bromide III was introduced into the Arbuzov reaction with trimethylsilyldiethylphosphite to yield phosphonate IV, deprotection of which with diluted hydrochloric acid resulted in the phosphorus analog of glutamic acid V.