SYNTHESIS OF O-GLYCOPYRANOSIDES WITH
POTENTIAL ANTIVIRAL ACTIVITY AGAINST
ZIKA, DENGUE AND CHIKUNGUNYA VIRUS
O-glycosides, 2-iodo-deoxy-O-glucosides, DIDMH.
This work aimed to synthesize and characterize novel O-glycosides and 2-iodo-deoxy-O-glycosides from D-glycals with various primary alcohols. Initially, compound BPSE 11 promoted the protection of tri-O-acetyl-D-glucal 12a to provide PSE-D-glucal 13a in 77% yield. This was followed by acetylation of the compound PSE- D-glucal 13a in 80% yield and oxidation in 82% yield. To obtain the O-glycosides, PSE-D-glycals 13a-b was used with the epoxidizing agents MCPBA and Oxone® in the presence of acetone in a basic medium to give compounds 14, 15a-b, 16a-b and 17a-b in good yields. In parallel, tri-Oacetyl-D-galactal 12b was prepared in 52% yield. Subsequently, the series of 2- iodo-deoxy-O-glycosides were prepared using the D-glycals 12a-b and 13a using the iodine reagent DIDMH at reflux and microwave irradiation, obtaining excellent yields