peracetate

Peracetate is a term used in organic and carbohydrate chemistry to refer to a compound in which all suitable functional groups have been converted to acetate esters. In particular, peracetates commonly describe fully acetylated derivatives of polyols, such as sugars, where every hydroxyl group is esterified with the acetyl group derived from acetic acid. For example, glucose pentaacetate is the peracetylated form of glucose.

Preparation typically involves treating the substrate with acetic anhydride (often with a base such as pyridine or DMAP as a catalyst) to promote acetylation. The resulting peracetate is usually more lipophilic and sometimes less reactive at the protected sites, facilitating selective reactions at remaining sites later in a synthesis.

Hydrolysis of a peracetate under acidic or basic conditions can remove the acetyl groups to regenerate the free hydroxyl groups.

Peracetates are widely used as protecting groups in organic synthesis, particularly in carbohydrate chemistry, to prevent multiple hydroxyl groups from participating in undesired reactions.

In some contexts, peracetate may also refer to salts or esters derived from peracetic acid; however, the most common usage relates to acetylated derivatives rather than peracetic acid salts.