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Issue 20, 1976
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A highly stereospecific synthesis of (R)- and (S)-[2-2H1]glycine

Abstract

Chirally pure [2-2H1]glycines were synthesised by the following sequence: O-benzylserine (4) 3-benzyloxy-2-bromopropionic acid (5) 3-benzyloxy[2-2H1]propionic acid (6) 3-benzyloxy[2-2H1]propionamide (7) 2-benzyloxy[1-2H1]ethylamine (8) 2-benzyloxy-N-phthaloyl[1-2H1]ethylamine (9) 2-hydroxy-N-phthaloyl[1-2H1]ethylamine (10)[2-2H1]glycine (13). The isotopic, chemical, and optical purity of these compounds was determined by microanalyses and mass, n.m.r., and o.r.d. spectra. Complete retention of configuration in the first and second steps was established by correlation with (S)-(–)-2-bromopropionic acid and by conversion into (+)-(S)-[2-2H1]propionic acid, respectively. (S)-O-Benzyl[2-3H1]serine was made, and can be used to prepare (S)-[2-3H1]glycine.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1976, 2229-2237
Article type
Paper

A highly stereospecific synthesis of (R)- and (S)-[2-2H1]glycine

W. L. F. Armarego, B. A. Milloy and W. Pendergast, J. Chem. Soc., Perkin Trans. 1, 1976, 2229
DOI: 10.1039/P19760002229

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