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Acetonide

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(Redirected from Isopropylidene acetal) Chemical compound
General structure of a 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. Acetonide is a common protecting group for 1,2- and 1,3-diols. The protecting group can be removed by hydrolysis of the ketal using dilute aqueous acid.

Example

The acetonides of small di- and triols, as well as many sugars and sugar alcohols, 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 + → 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.

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 Medical Publishers. p. 103.
  2. Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. (1998). "Configurational Assignment of Polyene Macrolide Antibiotics Using the Acetonide Analysis". Acc. Chem. Res. 31: 9–17. doi:10.1021/AR960223N.
  3. Christopher R. Schmid; Jerry D. Bryant (1995). "D-(R)-Glyceraldehyde Acetonide". Org. Synth. 72: 6. doi:10.15227/orgsyn.072.0006.
  4. Christian Hubschwerlen; Jean-luc Specklin; J. Higelin (1995). "L-(S)-glyceraldehyde Acetonide". Org. Synth. 72: 1. doi:10.15227/orgsyn.072.0001.
  5. Steinhilber, D; Schubert-Zsilavecz, M; Roth, HJ (2005). Medizinische Chemie (in German). Stuttgart: Deutscher Apotheker Verlag. p. 337. ISBN 3-7692-3483-9.
  6. Derendorf, H.; Hochhaus, G.; Meibohm, B.; Mollmann, H.; Barth, J. (1998). "Pharmacokinetics and Pharmacodynamics of Inhaled Corticosteroids". J. Allergy Clin. Immunol. 101: S440 – S446. doi:10.1016/S0091-6749(98)70156-3.
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