Synthesis of tetrahydropteridine C6-stereoisomers, including N5-formyl-(6S)-tetrahydrofolic acid

SW Bailey, RY Chandrasekaran…

Index: Bailey, Steven W.; Chandrasekaran, Rama Y.; Ayling, June E. Journal of Organic Chemistry, 1992 , vol. 57, # 16 p. 4470 - 4477

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Citation Number: 38

Abstract

Chiral N1-protected vicinal diamines derived from amino acids were condensed with 2- amino-6-chloro-5-nitro-4 (3H)-pyrimidhone, the nitro group reduced, and the amine deprotected. Oxidative cyclization of the resulting triaminopyrimidinone via quinoid pyrimidine intermediates gave a quinoid dihydropteridine, which was then reduced to a tetrahydropteridine C6-stereoisomer. Thus, 6 (R)-and 6 (S)-propyltetrahydropterin were ...