77390-82-0Relevant academic research and scientific papers
Purines, Pyrimidines, and Imidazoles. Part 57. Reactions of Some Oxazolino-xylofuranose Derivatives
Brown, Hopeton J.,Shaw, Gordon,Wright, David
, p. 657 - 660 (2007/10/02)
2'-Methyl-3,5-O-isopropylidene-α-D-xylofuranoso-Δ2'-oxazoline reacts with benzaldehyde, p-nitrobezaldehyde, and anisaldehyde to give 2'-styryl-, 2'-p-nitrostyryl-, or 2'-p-methoxystyryl-3,5-O-isopropylidene-α-D-xylofuranoso-Δ2'-oxazolines. 3,5-O-Isopropylidene-D-xylofuranosylamine with carbon disulphide gave 2'-mercapto-3,5-O-isopropylidene-α-Δ-xylofuranoso-Δ2'-oxazoline, methylation of which produced the 2'-methylthio-oxazoline, which was desulphurised to give 3,5-O-isopropylidene-α-D-xylofuranoso-Δ2'-oxazoline.The xylosylamine with p-tolylsulphonylaminoacetimidate and benzyloxycarbonylaminoacetimidate gave 2'-p-tolylsulphonylaminomethyl (or benzyloxycarbonylaminomethyl)-3,5-O-isopropylidene-α-D-xylofuranoso-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-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.
