methyl (2R)-2,3-dihydroxypropanoate

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

Procedure: The compound of Example 68-1 (308 mg, 2.57 mmol) was dissolved in methylene chloride (10 ml), and thereto were added triethylamine (704 mg, 6.95 mmol), 4-dimethylaminopyridine (33 mg, 0.27 mmol), and t-butyldimethylsilyl chloride (524 mg, 3.48 mmol). The mixture was stirred at room temperature for 2 hours, and thereto was added a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give the title compound (356 mg, 57%). The mixture was extracted with ethyl acetate the organic layer was washed with water and saturated saline dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the resulting residue was purified by silica gel column chromatography

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

Procedure: Pyridinium p-toluenesulfonate (50 mg) was added to a solution of 8.3 g of (R)-methyl glycerate in 30 ml of 2,2-dimethoxypropane and the mixture was refluxed for 30 minutes. The reaction mixture was purified by columnchromatography using silica gel (120 g) and hexane:ethyl acetate (5:1) as an eluant to give 9.87 g (89%) of (R)-methyl glycerate acetonide. the mixture was refluxed for 30 minutes The reaction mixture was purified by columnchromatography

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

Procedure: The compound of Example 68-1 (308 mg, 2.57 mmol) was dissolved in methylene chloride (10 ml), and thereto were added triethylamine (704 mg, 6.95 mmol), 4-dimethylaminopyridine (33 mg, 0.27 mmol), and t-butyldimethylsilyl chloride (524 mg, 3.48 mmol). The mixture was stirred at room temperature for 2 hours, and thereto was added a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give the title compound (356 mg, 57%). The mixture was extracted with ethyl acetate the organic layer was washed with water and saturated saline dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the resulting residue was purified by silica gel column chromatography

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

Procedure: Pyridinium p-toluenesulfonate (50 mg) was added to a solution of 8.3 g of (R)-methyl glycerate in 30 ml of 2,2-dimethoxypropane and the mixture was refluxed for 30 minutes. The reaction mixture was purified by columnchromatography using silica gel (120 g) and hexane:ethyl acetate (5:1) as an eluant to give 9.87 g (89%) of (R)-methyl glycerate acetonide. the mixture was refluxed for 30 minutes The reaction mixture was purified by columnchromatography

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

Procedure: The compound of Example 68-1 (308 mg, 2.57 mmol) was dissolved in methylene chloride (10 ml), and thereto were added triethylamine (704 mg, 6.95 mmol), 4-dimethylaminopyridine (33 mg, 0.27 mmol), and t-butyldimethylsilyl chloride (524 mg, 3.48 mmol). The mixture was stirred at room temperature for 2 hours, and thereto was added a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give the title compound (356 mg, 57%). The mixture was extracted with ethyl acetate the organic layer was washed with water and saturated saline dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the resulting residue was purified by silica gel column chromatography

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

Procedure: Pyridinium p-toluenesulfonate (50 mg) was added to a solution of 8.3 g of (R)-methyl glycerate in 30 ml of 2,2-dimethoxypropane and the mixture was refluxed for 30 minutes. The reaction mixture was purified by columnchromatography using silica gel (120 g) and hexane:ethyl acetate (5:1) as an eluant to give 9.87 g (89%) of (R)-methyl glycerate acetonide. the mixture was refluxed for 30 minutes The reaction mixture was purified by columnchromatography