Conformational analysis of sugars and their derivatives

Durette, Philippe L., and Horton, D Conformational Analysis of Sugars and Their Derivatives, 26,49-125 Dutcher, James D., Chemistry of the Amino Sugars Derived from Antibiotic Substances, 18, 259-308... 

Durette PL, Horton D. Conformational analysis of sugars and their derivatives. Adv Carbohydr Chem Biochem 1971 26 49-125. 

The study of the conformations of cyclic sugars was developed more fully by Reeves in a series of papers, beginning in 1949, dealing with the formation of complexes of sugars and their derivatives in cuprammonia solution. Reeves was able to provide experimental evidence to indicate that some pyranoid sugars indeed adopt chair conformations in solution, and that, in such cases, one chair form usually appeared to preponderate over the other. Boat or skew conformations were considered possible if the nonbonded interactions between the substituents in the chair conformation became too large. " Reeves s investigations have formed the basis of much subsequent work in the conformational analysis of cyclic carbohydrate... 

A notable exception has been the application of i.r. spectroscopy by Isbell and Tipson to the analysis of the conformations of methyl aldopyranosides," acetylated methyl aldopyranosides," " and fully acetylated aldopyranoses in the solid state. Their approach was based on (J) the assumption that the pyranoid sugar derivatives predicted by Reeves to exist in only one of the chair conformations in solution would adopt that same conformation in the crystalline state, and (2) the observation that axially and equatorially attached groups at the anomeric carbon atom give rise to different vibrations. 

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