Condensation of 2,4,5-triamino-6-butoxypyrimidine with various 2-formyloxiranes followed by oxidation with iodine affords 2-amino-4-butoxy-6-(1-hydroxyalkyl)pteridines regioselectively. Naturally occurring L-erythro-biopterin is synthesized from (1S,2S,3S)-2-formyl-3-(1-hydroxyethyl)oxirane. The reaction proceeds via 5,6-dihydropteridine, and the mechanism is discussed with the help of molecular orbital calculations.
All Science Journal Classification (ASJC) codes
- Organic Chemistry