Deoxy sugars nuclear magnetic resonance

Other methods of identification include the customary preparation of derivatives, comparisons with authentic substances whenever possible, and periodate oxidation. Lately, the application of nuclear magnetic resonance spectroscopy has provided an elegant approach to the elucidation of structures and stereochemistry of various deoxy sugars (18). Microcell techniques can provide a spectrum on 5-6 mg. of sample. The practicing chemist is frequently confronted with the problem of having on hand a few milligrams of a product whose structure is unknown. It is especially in such instances that a full appreciation of the functions of mass spectrometry can be developed. 

W. A. Szarek, A. Zamojski, A. R. Gibson, D. M. Vyas, and J. K. N. Jones, Selective, reductive dechlorination of chlorodeoxy sugars. Structural determination of chlorodeoxy and deoxy sugars by l3C nuclear magnetic resonance spectroscopy, Can. J. Chem. 54 3783 (1976). 

Nuclear Magnetic Resonance Data for Some Deoxy Sugar Derivatives... 

Several 4-deoxy-4-nitro ketose derivatives have been synthesized. Three crystalline 2,7-anhydro-4-deoxy-4-nitro-/3-D-heptulopyranoses arose by nitromethane cyclization92 of the dialdehyde (74) produced by periodate oxidation of sedoheptulosan (73), and were assigned93 the D-alio (75), D-gulo (76), and D-altro (77) configurations by nuclear magnetic resonance spectroscopy of the corresponding, peracetylated amino sugars. When the cyclization of 74 was performed in methan-olic medium, a solid mixture of stereoisomeric nitronates was obtained in almost quantitative yield, and it could be partially separated into the individual nitronates, which furnished 75 and 76. The isomer 77... 

L. D. Hall and J. F. Manville, Studies of carbohydrate derivatives by nuclear magnetic doubleresonance. Part I. Studies of deoxy-sugars by proton magnetic resonance spectroscopy, in S. Hanessian, (Ed.), Deoxy-Sugars, Advances in Chemistry Series, Vol. 74, American Chemical Society, Washington, DC, 1968, pp. 228-252. 

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