L-(S)-Glyceraldehyde acetonide (CAS NO.: ), which is known as -4-carboxaldehyde, 2,2-dimethyl-, L-, could be produced through the following synthetic route.

A 500-mL, four-necked, reaction flask, equipped with a mechanical stirrer, thermometer, and glass pH electrode combined with an automatic titrator, is charged with sodium (meta)periodate (85.5 g, 0.4 mol) and water (200 mL). The suspension is cooled to 0°C in an ice bath and 3 N sodium hydroxide (about 133 mL, 0.4 mol) is added dropwise at a rate such that the temperature does not exceed 7°C. The final pH of the suspension is 5.5. The cooling bath is removed and finely powdered 5,6-O-isopropylidene-L-gulono-1,4-lactone (43.6 g, 0.2 mol) is added in one portion. The temperature of the mixture is kept below 30°C. The pH of the suspension is maintained at 5.5 during the course of the reaction by addition of aqueous 15% sodium carbonate (about 15 mL). The suspension is further stirred at room temperature for 30 min, saturated with sodium chloride (105 g), and filtered by suction using a Büchner funnel. The white solid is washed thoroughly with two 50-mL portions of brine and the pH of the combined aqueous layers is adjusted to 6.7 with aqueous 15% sodium carbonate before extraction with dichloromethane (6 × 100 mL). The combined organic extracts are dried over magnesium sulfate (25 g). The magnesium sulfate is removed by filtration and washed with two 50-mL portions of dichloromethane. The organic solutions are combined and slowly concentrated to about 50 mL under reduced pressure. The remaining solution is placed in a 100-mL, round-bottomed flask equipped with a -coated magnetic stirring bar and a 10-cm, vacuum-jacketed, Claisen-Vigreux column (10-mm diameter). With constant stirring by a magnetic stirrer, the solution is further concentrated by distillation under reduced pressure (400 mbar) at 35°C (bath temperature). The temperature of the oil bath is then gradually increased to 80°C and the glyceraldehyde acetonide is distilled between 51°C and 52°C. The distillate is collected in a receiver cooled with an ice-methanol bath. Approximately 14.5 g of L-(S)-glyceraldehyde acetonide (56% based on 5,6-O-isopropylidene-L-gulono-1,4-lactone) is obtained.