ISSN:
0749-1581
Keywords:
1H NMR
;
13C NMR
;
15N NMR
;
2-methylthio-(glyco)oxazolines
;
ring size
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260241102
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