(S)-2-Acetoxypropionyl chloride

(S)-2-Acetoxypropionyl chloride is a chiral acid chloride used to introduce an acetyl-protected lactyl fragment. Its activated carbonyl forms amide or ester bonds, while the acetate masks the neighboring hydroxyl group during coupling. The established stereocenter transfers a defined lactate-derived configuration into the resulting acylated product.

The selected material is the S-configured acid chloride, rather than lactic acid or an unprotected hydroxy acid. The protected alcohol and reactive acyl group allow bond formation at the carbonyl without initially exposing the hydroxyl. Subsequent deacetylation gives access to alpha-hydroxypropionyl derivatives. This staged reactivity is useful when the lactyl unit must be attached before its alcohol participates in later transformations.

Typical Applications

• Protected lactyl amides: Used to acylate amino-containing substrates, introducing an S-configured acetoxypropionyl group that can later be converted into the corresponding hydroxy amide.
• Chiral lactate-derived esters: Used with alcohol-bearing intermediates to construct protected hydroxy-acid ester linkages, separating ester formation from later release of the alpha-hydroxyl group.

Specifications

Specifications describe the standard grade. Tolerance, test method and documentation package are confirmed per order.