Sorbose is a

ketose In organic chemistry, a ketose is a monosaccharide containing one ketone () group per molecule. The simplest ketose is dihydroxyacetone (), which has only three carbon atoms. It is the only ketose with no optical activity. All monosaccharide keto ...

belonging to the group of

sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecul ...

s known as

monosaccharide Monosaccharides (from Greek '' monos'': single, '' sacchar'': sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. Chemically, monosaccharides are polyhy ...

s. It has a sweetness that is equivalent to

sucrose Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula . For human consumption, sucrose is extracted and refined ...

(table sugar). The commercial production of

vitamin C Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits, berries and vegetables. It is also a generic prescription medication and in some countries is sold as a non-prescription di ...

(

ascorbic acid Ascorbic acid is an organic compound with formula , originally called hexuronic acid. It is a white solid, but impure samples can appear yellowish. It dissolves freely in water to give mildly acidic solutions. It is a mild reducing agent. Asco ...

) often begins with sorbose. L-Sorbose is the configuration of the naturally occurring sugar. It can be prepared from inexpensive O-benzylglucose.

Synthesis

Under conditions employed for a Meerwein-Ponndorf-Verley reduction, the tetra-O-benzyl aldose converts to tetra-''O''-benzylsorbose.

Hydrogenolysis Hydrogenolysis is a chemical reaction whereby a carbon–carbon or carbon–heteroatom single bond is cleaved or undergoes lysis (breakdown) by hydrogen.Ralph Connor, Homer Adkins. Hydrogenolysis Of Oxygenated Organic Compounds. J. Am. Chem. Soc. ...

removes the four

benzyl group In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure . Benzyl features a benzene ring () attached to a methylene group (). Nomenclature In IUPAC nomenclature, the prefix benzyl refers to a substituent, ...

s, leaving sorbose.

References

{{ketone-stub Ketohexoses