Syntheses and Coupling Reactions of 1,2-Anhydro-3,5-Di-O-Benzyl-α-L-Ribofuranose and 1,2-Anhydro-5-O-Benzyl-3-O-Methyl-α-L-Ribofuranose

Abstract 1,2-Anhydro-3,5-di-O-benzyl-α-L-ribofuranose (7) and 1,2-anhydro-5-O-benzyl-3-O-methyl-α-L-ribofuranose (20) were synthesized from L-arabinose via the key intermediates 3,5-di-O-benzyl-2-O-tosyl- (5) and 5-O-benzyl-3-O-methyl-2-O-tosyl-L-arabinofuranose (18) respectively. Condensation of the anhydro sugars with silylated uracil in the absence of catalyst gave the corresponding nucleoside derivatives with free 2′-OH in high yield. Selective glycosylation of 1,2-O-isopropylidene-α-D-xylofuranose with 7 afforded (1→5)-β-linked disaccharide predominantly in a good yield.

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