1407180-87-3Relevant academic research and scientific papers
Synthesis of substituted benzyl homo-C-ribonucleosides and -nucleotides as carba analogues of phosphoribosylanthranilate
Kubelka, Tomas,Slavetinska, Lenka,Hocek, Michal
, p. 4969 - 4981 (2013/01/14)
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. Novel benzyl C-nucleosides were designed and prepared as carba analogues of phosphoribosylanthranilate, an important intermediate in the biosynthesis of tryptophan. Copyright
