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
Title:
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
Author:
Ning, Jun Kong, Fanzuo
Appeared in:
Journal of carbohydrate chemistry
Paging:
Volume 16 (1997) nr. 3 pages 311-325
Year:
1997-03-01
Contents:
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.
Journal description