SYNTHESIS AND ANOMERIC CONFIGURATION OF 2-(ERYTHROFURANOSYL)BENZIMIDAZOLE C-NUCLEOSIDE ANALOGS

Anomeric 2-(alpha- and beta-D-erythrofuranosyl)benzimidazole C-nucleos ide analogues 2 and 3, were prepared from the corresponding epimeric 2 -(D-arabino, and D-ribo-tetritol-1-yl)benzimidazole analogues 1 and 4, respectively. Similarly, 2-(beta-L-erythrofuranosyl)benzimidazole 13 was obtained from the precursor 2-(L-arabino-tetritol-1-yl)benzimidazo le 12. The structure and anomeric configuration of the C-nucleoside an alogues 2, 3, and 13 were determined by acylation, H-1 and C-13 NMR sp ectroscopy, and mass spectrometry. (C) 1997 Elsevier Science Ltd.