acetonidelike
Acetonidelike is a term used in some chemical literature to describe motifs or protecting groups that resemble the acetonide (isopropylidene acetal) in structure or function. The canonical acetonide is formed by condensation of a vicinal diol with acetone, producing a five-membered cyclic acetal (1,3-dioxolane) bearing two methyl substituents from the acetone. When a group or protecting group behaves similarly—masking hydroxyl groups, limiting conformational flexibility, and increasing lipophilicity—it may be described as acetonidelike.
Acetonides are the most common acetonidelike motifs, but the concept can extend to analogous cyclic acetals
Acetonidelike protections are typically formed by acid-catalyzed acetalization of a vicinal diol with a carbonyl compound
In carbohydrate and natural product synthesis, acetonide protection is widely used to shield cis-diols and to