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- Title
Synthesis of Substituted Benzyl Homo- C-Ribonucleosides and -Nucleotides as Carba Analogues of Phosphoribosylanthranilate.
- Authors
Kubelka, Tomáš; Slavětínská, Lenka; Hocek, Michal
- Abstract
New 2-substituted benzyl C-ribonucleosides and -nucleotides were designed as carba analogues of phosphoribosylanthranilate, a key intermediate in tryptophan biosynthesis. The synthesis was based on the preparation of TBS-protected 2-bromobenzyl C-ribonucleoside 4a by addition of (2-bromobenzyl)magnesium bromide to ribonolactone followed by reduction and subsequent functional group transformations. Pd-catalyzed hydrogenation, cross-couplings, amination or hydroxylation, as well as lithiation followed by reaction with CO2 and amidations, gave a large series of 2-alkyl-, 2-(het)aryl, 2-amino, 2-hydroxy, 2-carboxy and 2-carbamoyl derivatives that were deprotected to afford free homo- C-ribonucleosides. Some of the title nucleosides were converted to 5′- O-phosphates.
- Publication
European Journal of Organic Chemistry, 2012, Vol 2012, Issue 26, p4969
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201200819