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1H , 13 C and 15 N NMR studies of 13 C and 15 N labeled 2‐methylthiooxazoline derivatives of pentoses and hexoses. Stereoelectronic effects on chemical shifts and mass fragmentation pathways
Author(s) -
Davidson Robert M.,
Byrd Gary D.,
White Edward,
Samm V,
Margolis A.,
Coxon Bruce
Publication year - 1986
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260241102
Subject(s) - chemistry , fragmentation (computing) , oxazoline , carbon 13 nmr , nuclear magnetic resonance spectroscopy , pentose , stereochemistry , chemical shift , mass spectrometry , aldose , organic chemistry , glycoside , operating system , chromatography , computer science , fermentation , catalysis
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 13 C‐ or 15 N‐labeled thiocyanates yielded either 2‐ 13 C‐labeled or 3‐ 15 N‐labeled derivatives. The structures of the products have been studied by 1 H, 13 C and 15 N 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.