Title: Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis
VOLUME: 6 ISSUE: 9
Author(s):Frank Seela and Xiaohua Peng
Affiliation:Laboratorium fur Organischeund Bioorganische Chemie, Institut fur Chemie, Universitat Osnabruck,Barbarastr. 7, D-49069 Osnabrück, Germany, and Center forNanotechnology (CeNTech), Gievenbecker Weg 11, 48149 Munster,Germany.
Keywords:7-deazapurine, pyrrolo[2,3-d]pyrimidine, ribonucleoside, glycosylation, C-nucleoside, L-nucleoside, natural occurrence, pharmacological properties
Abstract: This review reports on the synthesis of 7-deazapurine ribonucleosides, including C-nucleosides, 2-C-methyl derivatives and L-enantiomers. It covers the various aspects of convergent nucleoside synthesis such as the Schiff base procedure, the fusion reaction, the metal salt procedures, the Silyl-Hilbert-Johnson reaction, and the nucleobase anion glycosylation. The review discusses the scope and limitations of glycosylation reactions performed on 7-deazapurines. Peracylated ribose derivatives were now employed in the glycosylation, which overcome difficulties reported earlier.
