Abstract
The alkylation of 2-amino-6-chloropurine and of 2-amino-6-methylthiopurine with 1-bromo-2,2-diethoxyethane in dimethylformamide in the presence of sodium hydride has yielded 2-amino-6-chloro-9-(2′,2′-diethoxyethyl)purine and 2-amino-9-(2′,2′-diethoxyethyl)-6-methylthiopurine. By further transformations of these acetals, 6-substituted 2-aminopurin-9-ylacetaldehydes have been prepared from which, by the cyanohydrin synthesis β-(2-amino-6-hydroxypurin-9-yl)-α-alanine (guanin-9-yl-α-alanine) and β-(2-amino-6-mercaptopurin-9-yl)-α-alanine have been obtained. The synthesis of guanin-9-yl-α-alanine has completed the preparation of a series of α-alanine derivatives of the five most important heterocyclic bases present in RNA and DNA.
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Lidak, M.Y., Shluke, Y.Y., Poritere, S.E. et al. Synthesis of β-(2-aminopurin-9-yl)-α-alanines. Chem Heterocycl Compd 6, 490–493 (1970). https://doi.org/10.1007/BF00478399
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DOI: https://doi.org/10.1007/BF00478399