(2S)-4-phenylmethoxybutane-1,2-diol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-4-O-Benzyl-1,2,4-butanetriol (68.3 g, 348 mmol) was mixed with triethylamine (70.4 g, 696 mmol) and dimethylaminopyridine (3.42 g, 28 mmol) were mixed in methylene chloride (300 mL) under nitrogen atmosphere. To the solution p-anisylchlorodiphenylmethane (129.1 g, 418 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 5 hours. Saturated sodium bicarbonate was added to the mixture and the resulting mixture was stirred at room temperature for 1 hour. The aqueous layer was extracted with methylene chloride (150 mL×2). The combined methylene chloride extracts were dried over mganesium sulfate. The solvent was evaporated, and the residue was purified by flash chromatography on silica gel (ethyl acetate:hexane=1:5 to 1:1) to give 155.5 g (95% yield) of the title compound as a thick oil. at room temperature for 5 hours the resulting mixture was stirred at room temperature for 1 hour The aqueous layer was extracted with methylene chloride (150 mL×2) The combined methylene chloride extracts were dried over mganesium sulfate The solvent was evaporated the residue was purified by flash chromatography on silica gel (ethyl acetate:hexane=1:5 to 1:1)

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-2,2-Diisopropyl-4-(2-hydroxyethyl)dioxolane (76.2 g, 0.377 mol), benzylbromide (129 g, 0.753 mol) and tetrabutylammonium iodide (7 g, 19 mmol) were mixed with a concentrated sodium hydroxide solution (40 g in 90 mL of water, 2.26 mol) in a 3-neck flask equipped with a mechanic stirrer and a condenser. After stirred at 110° C. for 18 hours, the mixture was cooled to room temperature and the organic layer was separated. The aqueous layer was extracted with methylene chloride (100 mL×2). The combined methylene chloride extrats were dried over magnesium sulfate. The solvent was evaporated, and the residue was treated with 300 mL of 1.5M sulfuric acid. After stirred at 100° C. for 8 hours, the mixture was cooled to room temperature, and hexane (300 mL) was added. The aqueous layer was washed with hexane twice (200 mL×2), and then ajusted pH to 8-9 with concentrated sodium sodium hydroxide. The solution was extrated with ethyl acetate (200 mL×3). The combined ethyl acetate extrates were dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by fractional distillation in vacuo (0.1 mmHg, bp 150°-170° C.) to give 68.3 g (92% yield) of the title compound as an oil. equipped with a mechanic stirrer and a condenser the mixture was cooled to room temperature the organic layer was separated The aqueous layer was extracted with methylene chloride (100 mL×2) The combined methylene chloride extrats were dried over magnesium sulfate The solvent was evaporated the residue was treated with 300 mL of 1.5M sulfuric acid After stirred at 100° C. for 8 hours the mixture was cooled to room temperature hexane (300 mL) was added The aqueous layer was washed with hexane twice (200 mL×2) The combined ethyl acetate extrates were dried over magnesium sulfate The solvent was evaporated the residue was purified by fractional distillation in vacuo (0.1 mmHg, bp 150°-170° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In toluene (100 ml) were dissolved (S)-4-benzyloxy-1,2-butanediol (25.8 g, 0.132 mol), triethylamine (20.2 ml, 0.145 mol) and 4-N,N-dimethylaminopyridine (DMAP) (0.80 g, 6.58 mmol). After cooling in ice bath, trityl chloride (36.69 g, 0.1316 mol) was added to the solution and the mixture was stirred at room temperature for 10 hours. The mixture was condensed in vacuo, diluted with ethyl acetate, washed with water and then saturated brine, dried on sodium sulfate, filtered and condensed in vacuo to give (S)-4-benzyloxy-1-trityloxy-2-butanol quantitatively (55.89, yield 100%). After cooling in ice bath condensed in vacuo washed with water saturated brine, dried on sodium sulfate filtered condensed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In methanol (50 ml) were dissolved (S)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane (2.06 g, 8.73 mmol) and p-toluenesulfonic acid hydrate (1.68 g, 8.8 mmol), and the solution was stirred at room temperature for 24 hours. After removal of methanol in vacuo, aqueous saturated sodium hydrogen carbonate was added to neutralize the solution. The solution was extracted with ethyl acetete and the extract was washed with saturated brine, dried on sodium sulfate, filtered, and condensed in vacuo. The residue was subjected to silica gel chromatography to give (S)-4-benzyloxy-1,2-butanediol (1.70 g, yield 99%). After removal of methanol in vacuo, aqueous saturated sodium hydrogen carbonate was added The solution was extracted with ethyl acetete the extract was washed with saturated brine dried on sodium sulfate filtered condensed in vacuo