2,3-O-Isopropylidene-D-glyceraldehyde (CAS NO.: ), which is known as L-(S)-Glyceraldehyde acetonide, could be produced through the following synthetic routes.

A. 1,2:5,6-Diisopropylidene-D-mannitol. A 1-L, three-necked flask equipped with overhead stirrer, heating mantle, and condenser with drying tube is charged with 100 g of D-mannitol (0.549 mol), 240 mL of freshly-distilled 1,2-dimethoxyethane, and 160 mL of 2,2-dimethoxypropane (1.3 mol). Stirring is begun and 0.1 g of stannous chloride is added. The remaining neck is capped with a septum and the stirred slurry is heated to reflux. Reflux is maintained until the mixture becomes clear (30–50 min) and is continued for 30 min after clarity is attained. The heating mantle is removed and the solution is cooled below reflux. (200 μL) is added through the septum via syringe. After the solution is cooled to room temperature, it is transferred to a tared, 1-L, one-necked flask, and the contents are concentrated on a rotary evaporator, beginning at room temperature and increasing the temperature to 95–100°C. The flask contents are held at that temperature until no more evaporate is collected (15–30 min). The semi-solid is then cooled to room temperature, to yield 130–160 g of crude solid product of 50–55% purity (72–80 g, 50–56% yield) as assayed by 1H NMR against dichloromethane.

B. 2,3-O-Isopropylidene-D-glyceraldehyde (CAS NO.: ). A large, magnetic stir bar is added to the flask that contains the crude solid diacetonide from procedure A above and 700–800 mL of dichloromethane (10 mL/g of diacetonide) is added. The flask is equipped with a condenser and heating mantle, and the slurry is stirred vigorously and heated to reflux until the solids are digested to an even consistency. The mantle is removed, the slurry is allowed to cool below reflux, and Celite (10 g) is added with stirring. The contents are further cooled to room temperature and vacuum-filtered through a pad of Celite on a glass frit filter into a three-necked, 2-L vessel. The flask is rinsed with 50 mL of dichloromethane and the rinse is filtered through the funnel. The 2-L vessel is then equipped with an overhead stirrer, thermometer, and water bath, and stirring is begun at 300–350 rpm. A solution of 30–40 mL of saturated aqueous sodium bicarbonate (0.4 mL/g of diacetonide) is added with stirring, followed by 130–140 g of sodium metaperiodate (2.0 mol equiv), added portionwise over 2–3 min. The resulting mixture is stirred while the internal temperature is maintained below 35°C with water bath cooling. After the solution is stirred for 2 hr, 35–50 g of magnesium sulfate (0.5 g/g of diacetonide) is added and stirring is continued for 20 min. The slurry is vacuum-filtered through a glass frit filter into a 2-L, one-necked, round-bottomed flask. The filter cake is removed, transferred back into the three-necked vessel, 200 mL of dichloromethane is added, and the resulting slurry is stirred for 10 min. The slurry is vacuum-filtered and the filtrate is added to the one-necked flask.

The filtrate-containing flask is equipped with a 12"-Vigreux column, distillation head, receiver, and heating mantle, and dichloromethane is removed by distillation (head temperature to 40°C). The residual oil is cooled and transferred to a 250-mL, round-bottomed flask and the flask is equipped with a simple distillation head, cow receiver, and heating mantle. After a brief forerun (2–3 g), product is collected by distillation at 30 mm (65–120°C) into a chilled receiver (5°C) to afford 54–68 g (75–85%) of crude 2,3-O-isopropylidene-D-glyceraldehyde. The crude product is transferred to a 100-mL, round-bottomed flask equipped with a 6"-Vigreux column, cow receiver, and heating mantle, and redistilled at 30 mm, collecting the fraction distilling at 67–73°C into a chilled receiver to afford 50–64 g of product (70–80%, 34–45% overall).