Syntheses of highly functionalised 6-substituted pteridines
Guiney, D. and Gibson, C.L. and Suckling, C.J. (2003) Syntheses of highly functionalised 6-substituted pteridines. Organic and Biomolecular Chemistry, 1 (4). pp. 664-675. ISSN 1477-0520
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Methods for the synthesis of polyfunctional 6-substituted pteridines from the corresponding 6-aldehydes are described. Alkene, ester, ketone, amide, cyano, oxime, bromo, methoxy and dihydroxy functional groups have all been introduced principally through improved methodologies for Wittig reactions using 2-thioalkyl-6-formylpteridines as substrates. Further modification of the alkenes derived from the Wittig reactions was difficult but selective conversion to the vic-diol was possible using ligand assisted catalysis with osmium tetraoxide. These methods are a component of an extensive methodology for the preparation of compounds that might serve as modulators of tetrahydrobiopterin activity or as inhibitors of dihydroneopterin aldolase.
ORCID iDs
Guiney, D., Gibson, C.L.
Item type: Article ID code: 887 Dates: DateEvent3 January 2003PublishedKeywords: polyfunctional 6-substituted pteridines, 6-aldehydes, Alkene, ester, ketone, amide, cyano, oxime, bromo, methoxy, 2-thioalkyl-6-formylpteridines, osmium tetraoxide, dihydroneopterin aldolase, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry Subjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Allison Crawford Date deposited: 26 Apr 2006 Last modified: 19 Mar 2021 04:41 URI: https://strathprints.strath.ac.uk/id/eprint/887