Synthesis and radical polymerization behavior of N-vinylsaccharin (1) are described. Radical homopolymerization of 1 was carried out in the presence of a radical initiator for 24 h to afford the polymer containing a saccharin moiety in the side group, which was insoluble in common organic solvents. Among the copolymers of 1 with various vinyl monomers such as vinyl acetate (VAc), methyl acrylate (MA), acrylonitrile (AN), and styrene (St), only the copolymer [copoly(1-St)] obtained from 1 and St was soluble in common organic solvents. In the copolymerization of 1 and St, the Q and e values of 1 were estimated to be 0.10 and Ϫ1.60, respectively. These values are similar to those of N-vinylphthalimide (Q ϭ 0.36, e ϭ Ϫ1.52). The reaction of copoly(1-St) with LiAlH 4 was carried out in THF for 24 h to convert the saccharin moiety into the ring-opened structure bearing hydroxy and sulfonamide groups.
A method for the protecting group free synthesis of β-urea-linked glycoconjugates has been developed. The one step process, involving reactions between urea and D-glucose, N-acetyl-D-glucosamine or D-xylose in acidic aqueous solution, furnishes the corresponding β-urea glycosides in modest yields. This simple and efficient procedure is applicable to the synthesis of β-urea tethered amino acid-carbohydrate conjugates.
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