Magnetic Resonance in Chemistry p. 929 - 937 (1986)
Update date:2022-08-16
Topics:
Davidson, Robert M.
Byrd, Gary D.
White, Edward
Margolis, Sam A.
Coxon, Bruce
A facile synthesis of 2-methylthio-(glyco)oxazoline derivatives has been developed which involves methylation of 2-thiono-(glyco)oxazolidines prepared by condensation of aldoses with thiocyanate ion.The synthesis has been applied to the preparation of six 2-methylthiooxazoline derivatives in the pentose series and six derivatives in the hexose series.For several sugars, both pyranoid and furanoid forms were isolated, and the use of either 13C- or 15N-labeled thiocyanates yielded either 2-13C-labeled or 3-15N-labeled derivatives.The structures of the products have been studied by 1H, 13C and 15N NMR spectroscopy and by electron-impact and field desorption mass spectrometry.Multinuclear chemical shift correlations and analyses of fragmentation pathways have facilitated the assignment of ring size in the 2-methylthio-(glyco)oxazoline derivatives.KEY WORDS 1H NMR, 13C NMR, 15N NMR, 2-methylthio-(glyco)oxazolines, ring size
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