Acetonide

General structure of an 1,2-acetonide. The diol is shown in blue, the acetone part in red.

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

Examples

Corticosteroid acetonides are used pharmaceutically, especially in dermatology, because their increased lipophilicity leads to better penetration into the skin.[2]

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.

See also

References

  1. ↑ Kocieński, Philip j. (1994). "3.2.2: Diol Protecting Groups—Acetals—Isopropylidene Acetals". Protecting Groups. Foundations of Organic Chemistry Series. Thieme. p. 103.
  2. ↑ Steinhilber, D; Schubert-Zsilavecz, M; Roth, HJ (2005). Medizinische Chemie (in German). Stuttgart: Deutscher Apotheker Verlag. p. 337. ISBN 3-7692-3483-9.


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