Acetonide

In organic chemistry, an acetonide is the functional group composed of the cyclic compound ketal of a diol with acetone. The more systematic name for this structure is an ketal. Acetonide is a common protecting group for 1,2- and 1,3-. The protecting group can be removed by hydrolysis of the ketal using dilute aqueous acid.

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Example The acetonides of small di- and triols, as well as many and , are common. The hexaol mannitol reacts with 2,2-dimethoxypropane to give the bis-acetonide, which oxidizes to give the acetonide of glyceraldehyde:

(CHOHCHOHCH₂OH)₂ + 2 (MeO)₂CMe₂ → (CHOHCHCH₂O₂CMe₂)₂ + 4 MeOH

(CHOHCHOCH₂OCMe₂)₂ + O → 2 OCHCHCH₂O₂CMe₂ + H₂O

An example of its use as a protecting group in a complex organic synthesis is the Nicolaou Taxol total synthesis. It is a common protecting group for sugars and sugar alcohols, a simple example being solketal.

The acetonides of corticosteroid are used in dermatology, because their increased lipophilicity leads to better penetration into the skin.

• Fluclorolone acetonide
• Fluocinolone acetonide
• Triamcinolone acetonide

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See also

• Acetophenide
• Acroleinide
• Aminobenzal
• Cyclopentanonide
• Pentanonide

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