Carbohydrate-based approach to four enantiomerically pure 2-naphthylmethyl 3-hydroxy-2-methylbutanoates

Chiral pool approach using d-glucose, l-xylose, and d- and l-arabinoses was used to obtain four stereoisomeric 3-hydroxy-2-methylbutanoic acids with well defined configurations. The acids were isolated as fluorescent 2-naphthylmethyl esters after reaction with 2-naphthyldiazomethane.

The synthesis of the four stereoisomers of 3-hydroxy-2-methylbutanoic acid from carbohydrate precursors is described.