Synthesis of p-nitrobenzyl and p-nitrophenyl 1-thioglycopyranosides.
Reaction of 2,3,4-trio-O-acetyl-alpha-L-fucopyranosyl bromide (1) with thiourea (2), followed by reductive cleavage of the product, gave 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranose (4). Reaction of 4 with p-nitrobenzyl bromide followed by O-deacylation yielded p-nitrobenzyl 1-thio-beta-L-fucopyranoside (6). Similar reaction conditions were used for the synthesis of p-nitrobenzyl 1-thio-beta-D-fucopyranoside (11) and 1-thio-alpha-D-mannopyranoside (16). A facile preparation of O-acylated p-nitrophenyl 1-thioglycopyranosides was achieved by condensing the appropriate glycosyl halide with sodium p-nitrobenzenethioxide in N,N-dimethylformamide.
D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D009574:Nitro Compounds / Q000138:chemical synthesis; D009904:Optical Rotation; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D013865:Thioglycosides / Q000138:chemical synthesis*
D009574:Nitro Compounds; D013865:Thioglycosides