The acetonides of small di- and triols, as well as many
sugars and
sugar alcohols, are common.[2] The hexaol
mannitol reacts with
2,2-dimethoxypropane to give the bis-acetonide, which oxidizes to give the acetonide of glyceraldehyde:[3][4]
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.
^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.
^Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. (1998). "Configurational Assignment of Polyene Macrolide Antibiotics Using the [13c]Acetonide Analysis". Acc. Chem. Res. 31: 9–17.
doi:
10.1021/AR960223N.
^Christopher R. Schmid; Jerry D. Bryant (1995). "D-(R)-Glyceraldehyde Acetonide". Org. Synth. 72: 6.
doi:
10.15227/orgsyn.072.0006.
^Steinhilber, D; Schubert-Zsilavecz, M; Roth, HJ (2005). Medizinische Chemie (in German). Stuttgart: Deutscher Apotheker Verlag. p. 337.
ISBN3-7692-3483-9.