Synthesis of Substituted Benzyl Homo-C-Ribonucleosides and -Nucleotides as Carba Analogues of Phosphoribosylanthranilate
2012
Abstract
Title 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 preparation of TBS-protected 2-bromobenzyl-C-ribonucleoside by addition of 2-bromobenzylmagnesium bromide to ribonolactone followed by reduction and its follow-up functional group transformations.
Some of the title nucleosides were converted to 5'-O-phosphates.