Sequential Removal of Monosaccharides from the Reducing End of Oligosaccharides. 2. Fundamental Studies of a Reaction between Hydrazino Compounds and Sugars Having a Glycosyl Moiety on a Carbon Atom Adjacent to a Carbonyl Group

Article abstract of DOI:10.1021/jo00130a026

Hydrazine and certain hydrazino derivatives react with sugars having a glycosidic substituent, where the glycosyl moiety is located on a carbon atom adjecent to an aldehyde or keto group of the aglycon, resulting in cleavage of the glycosidic linkage.The reaction proceeds whether the glycon is of the α or β configuration.The released glycosyl moiety, in the presence of excess hydrazino compound, reacts further to give a hydrazone derivative.Removal of the hydrazone group gives the reducing sugar derived from the glycon.