Über Pterinchemie. 85. Mitteilung. Polyacetylierte 5,6,7,8-Tetrahydro-D- und -L-neopterine. Ein besonderer Fall vonN(5)-Alkylierung des 5,6,7,8-Tetrahydroneopterin-Gerüstes

Autor: Syméon Antoulas, Roland Prewo, Jost H. Bieri, Max Viscontini
Rok vydání: 1986
Předmět:
Zdroj: Helvetica Chimica Acta. 69:210-220
ISSN: 0018-019X
Popis: Polyacetylated 5,6,7,8-Tetrahydro-D- and L-neopterins. A Special Case of N(5)-Alkylation of 5,6,7,8-Tetrahydroneopterins Improved conditions are reported for the preparation of the earlier described (6R)- and (6S)-1′-O,2′-O,3′-O,2-N,5-pentaacetyl-5,6,7,8-tetrahydro-L-neopterins, one of which could be obtained as pure crystals. Its structure, determined by X-ray-diffraction analysis, corresponds to the (6R)-enantiomer. The method has also been used to make the corresponding D-diastereoisomers. Further acetylation of (6RS)-1′-O,2′-O,3′-O,2-N-tetraacetyl-5,6,7,8-tetrahydro-D-neopterin under drastic conditions yields a mixture of several polyacetylated D-neopterin derivatives and a polyacetylated ethyl-tetrahydro-D-neopterin which was isolated in crystalline form and established by X-ray-diffraction analysis to be (6R)-1′-O,2′-O,3′-O,4-O,2-N,2-N,8-heptaacetyl-5-ethyl-5,6,7,8-tetrahydro-D-neopterin.
Databáze: OpenAIRE