Dfructofuranoside

D-fructofuranoside refers to glycosides in which D-fructose, in its furanose form, serves as the glycone and the anomeric carbon of the fructose ring is bonded to a glycosidic aglycone. In this context, the bond typically forms at the anomeric C-2 of the fructofuranose ring, and the compound can exist as alpha- or beta-D-fructofuranoside derivatives depending on the orientation of the aglycone.

The class encompasses a range of alkyl, aryl, or other substituents attached through the glycosidic oxygen. Common examples include methyl D-fructofuranoside, and its ethyl, benzyl, or phenyl counterparts. The nomenclature indicates both the sugar moiety (D-fructose in furanose form) and the identity of the glycosyl substituent. The stereochemistry at the anomeric center may be specified as alpha or beta where relevant.

Preparation of D-fructofuranosides is typically achieved by glycosylation of D-fructose with an alcohol under acidic catalysis, or through protective group strategies that enable selective formation of the glycosidic bond at C-2. Hydrolysis of a D-fructofuranoside regenerates D-fructose and the corresponding aglycone, restoring the reducing sugar when appropriate conditions are applied.

Uses are chiefly in carbohydrate chemistry, where D-fructofuranosides serve as stable glycoside derivatives for studying glycosylation reactions, as protecting-group intermediates, or as synthetic building blocks. Methyl D-fructofuranoside, in particular, is a widely used standard reference compound and a convenient starting point for preparing more complex fructoside structures.

See also: glycoside, fructose, furanose, glycosylation.