Purines, pyrimidines, and imidazoles. Part 57. Reactions of some oxazolino-xylofuranose derivatives

Abstract

2′-Methyl-3,5-O-isopropylidene-α-D-xylofuranoso[1,2-d]-Δ²′-oxazoline reacts with benzaldehyde, p-nitrobenzaldehyde, and anisaldehyde to give 2′-styryl-, 2′-p-nitrostyryl-, or 2′-p-methoxystyryl-3,5-O-isopropylidene-α-D-xylofuranoso[1,2-d]-Δ²′-oxazolines. 3,5-O-Isopropylidene-D-xylofuranosylamine with carbon disulphide gave 2′-mercapto-3,5-O-isopropylidene-α-Δ-xylofuranoso[1,2-d]-Δ²′-oxazoline, methylation of which produced the 2′-methylthio-oxazoline, which was desulphurised to give 3,5-O-isopropylidene-α-D-xylofuranoso[1,2-d]-Δ²′-oxazoline. The xylosylamine with p-tolylsulphonylaminoacetimidate and benzyloxycarbonylaminoacetimidate gave 2′-p-tolylsulphonylaminomethyl (or benzyloxycarbonylaminomethyl)-3,5-O-isopropylidene-α-D-xylofuranoso[1,2-d]-Δ²′-oxazolines respectively. The tolylsulphonylaminomethyl-oxazoline with hydrogen sulphide gave 3,5-O-isopropylidene-N-(N-p-tolylsulphonylthioglycyl)-D-xylofuranosylamine which with methanesulphonyl chloride gave 3,5-O-isopropylidene-2′-(p-tolylsulphonylaminomethyl)-α-D-xylofuranoso[1,2-d]-Δ²′-thiazoline. Reaction of the p-tolylsulphonylaminomethyl- or benzyloxycarbonylaminomethyl-oxazolines with hydroxylamine gave corresponding 3,5-O-isopropylidene-D-xylofuranosylamidoximes, whereas with ammonia the sugar unit was cleaved and simple glycinamidines obtained. The structures assigned were confirmed by analytical, u.v., n.m.r., and mass-spectral techniques.