Purines, Pyrimidines, and Imidazoles. Part 57. Reactions of Some Oxazolino-xylofuranose Derivatives

DOI: 10.1039/P19810000657

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 657 - 660 (1981)

Update date:2022-08-04

Topics:

Authors:

Brown, Hopeton J.

Shaw, Gordon

Wright, David

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Article abstract of DOI:10.1039/P19810000657

2'-Methyl-3,5-O-isopropylidene-α-D-xylofuranoso<1,2-d>-Δ^2'-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<1,2-d>-Δ^2'-oxazolines. 3,5-O-Isopropylidene-D-xylofuranosylamine with carbon disulphide gave 2'-mercapto-3,5-O-isopropylidene-α-Δ-xylofuranoso<1,2-d>-Δ^2'-oxazoline, methylation of which produced the 2'-methylthio-oxazoline, which was desulphurised to give 3,5-O-isopropylidene-α-D-xylofuranoso<1,2-d>-Δ^2'-oxazoline.The xylosylamine with p-tolylsulphonylaminoacetimidate and benzyloxycarbonylaminoacetimidate gave 2'-p-tolylsulphonylaminomethyl (or benzyloxycarbonylaminomethyl)-3,5-O-isopropylidene-α-D-xylofuranoso<1,2-d>-Δ^2'-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>-Δ^2'-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.