Anomeric Bond-Character in the Pyranose Sugars

Evidence from determinations of crystal structure relating to the shortening of carbon-oxygen bonds in the anomeric position in pyranose sugars is presented. There is a high degree of probability that the C(1)-O(1) bond is shortened by about 0.04 A relative to the other C-O single-bond lengths, except in the case of an axially oriented glycosidic group where there is evidence of a distinction between the two ring C-O bonds.