98044-35-0Relevant academic research and scientific papers
Synthesis of N-unsubstituted, mono- and disubstituted carbohydrate-1-O- carbamates and their behaviour in glycoside syntheses
Knoben, Hans-Peter,Schlüter, Urs,Redlich, Hartmut
, p. 2821 - 2833 (2007/10/03)
The syntheses of 44 1-carbamates from six different 1-O-unprotected carbohydrate derivatives (compounds 1-6), representing typical protecting pattern in glycoside synthesis, are described. The carbamate function is N-unsubstituted (compounds 1b-6b), mono-
Uridine 5'-diphosphate glucose analogues. Inhibitors of protein glycosylation that show antiviral activity
Camarasa,Fernandez-Resa,Garcia-Lopez,De las Heras,Mendez-Castrillon,Alarcon,Carrasco
, p. 40 - 46 (2007/10/02)
A series of analogues of uridine 5'-diphosphate glucose and uridine 5'-diphosphate glucosamine have been synthesized by reaction of 2,3,4,6-tetra-O-benzyl-, 2,3,4,6-tetra-O-benzoyl-, 2,3,4,6-tetra-O-acetyl-, and 2,3,4,6-tetra-O-palmitoyl-α-D-glucopyranose and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose with chlorosulfonyl isocyanate and 2',3'-O-isopropylideneuridine. Isopropylidene and acetyl groups of the resulting 5'-O-[[[[(α-D-glucopyranosyl)oxy]carbonyl]amino]sulfonyl]-2',3'-O-isoprop ylideneuridine derivatives were removed by reaction with a TFA/water (5:1) mixture and methanolic ammonia, respectively. The 5'-O-[[[[(2'',3'',4'',6''-tetra-O-benzyl- and 2'',3'',4'',6''-tetra-O-benzoyl-α-D-glucopyranosyl)oxy]carbonyl]amino]sul fonyl]-2',3'-O-isopropylideneuridine (13 and 19) and the corresponding deisopropylidenated derivatives showed antiviral activity as determined by the inhibition of the cytopathic effect induced by HSV-1 replication and by the plaque assay method. Compound 13 inhibited glycosylation of proteins in HSV-1 infected HeLa cells.
