A procedure for preparing anhydropentitol mono, di, and tri esters is described. The process is performed in a single vessel and involves sequential dehydrative cyclization and carboxylic acid acylation steps. Each step is catalyzed by low loadings of a water-tolerant Lewis acid catalyst. The method of synthesis is efficacious and depending on the reaction condition, generates modest to high yields of the target mono-, di-, and triesters. The esters can be practical surrogates of incumbent petroleum materials of similar structure used for surfactants and plasticizers.