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- Title
Pteridine. Teil XCIV. Synthese und Eigenschaften von 5,6-Dihydro-6-(1,2,3-trihydroxypropyl)pteridinen: Kovalente intramolekulare Addukte.
- Authors
Soyka, Rainer; Pfleiderer, Wolfgang; Prewo, Roland
- Abstract
Pteridines: Synthesis and Characteristics of 5,6-Dihydro-6-(1,2,3-trihydroxypropyl)pteridines: Covalent Intramolecular Adducts Various 5,6-diaminopyrimidines ( 1, 15, 24, 33) were condensed with the phenylhydrazones of L-( 2) and D-arabinose ( 3) in acidic medium under N2 to give formal 5,6-dihydro-6-(1,2,3-trihydroxypropyl)pteridines (see, e.g., 4 and 5), the latter turned out to exist preferentially as intramolecular adducts, the hexahydropyrano-[3,2- g]pteridines 6, 7, 16, 17, 25, 26, and 34, formed subsequently by addition of the terminal OH group of the side-chain to the C(7)N(8) bond of the pteridine moiety. Spectroscopically, the isomeric hexahydrofuro-[3,2- g]pteridines 10,11,18,19, and 35 were also detected as minor components in the equilibrium mixtures. In the 4-amino-2-(methylthio)pteridine series, crystallization of 6 and 7 led to the stereochemically pure (3 S,4 R,4a R, 10a S)-6-amino-3,4,4a,5,10,10a-hexahydro-8-(methylthio)-2 H-pyrano[3,2- g]pteridine-3,4-diol ( 8) and its corresponding enantiomer 9, respectively Structure 8 was proven by X-ray analysis. Acylation of the hexahydropyrano[3,2- g]pteridines yielded the more stable tri-, tetra-, and pentaacetyl derivatives 12-14, 20-23, 27-32, and 37-39 which were characterized and of which the absolute and relative configurations were determined (1H- and 13C-NMR and UV spectra, chiroptical measurements, elemental analyses).
- Publication
Helvetica Chimica Acta, 1990, Vol 73, Issue 4, p808
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19900730407