3-phenylmethoxypropane-1,2-diol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of 10.0 g (0.055 mol) of DL-α-O-benzylglycerol in a little THF was added to a suspension of 15.38 g (0.137 mol) of potassium tert-butoxide in 300 mL of THF. The mixture was stirred for 1 hr at RT and 18.72 (0.132 mol) of iodomethane was added. A white solid immediately separated. The reaction was stirred for 10 hr at RT, cooled, carefully diluted with sodium chloride solution and extracted with ether. The organic layer was washed with water, 5% HCl, water and saturated NaCl and dried. The solvent was removed and the residue was purified by flash chromatography to give 1-benzyloxy-2,3-dimethoxypropane, 9.16 g (79%), as an oil. A white solid immediately separated The reaction was stirred for 10 hr at RT cooled carefully diluted with sodium chloride solution extracted with ether The organic layer was washed with water, 5% HCl, water and saturated NaCl dried The solvent was removed the residue was purified by flash chromatography

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

Procedure: 1-O-Oleoyl-2-O-methyl-rac-glycerol (Compound 44) To a mixture of 1-O-benzyl-glycerol (27 mL, 0.16 mol) and t-butyldimethylsilyl chloride (25 g, 0.17 mol) in dry CH2Cl2 (250 mL) under N2 was added DMAP (0.8 g, 6.6 mmol) followed by the addition of TEA (23 ml, 0.17 mol). After 3 hours, the mixture was washed with H2O (2×100 mL), dried (MgSO4) and concentrated to give 1-O-benzyl-3-O-t-butyldimethylsilyl-rac-glycerol (40) (48.8 g, 100%) as a yellow oil. 1H NMR (360 MHz; CDCl3): (0.06 (6H, s, Me2Si), 0.89 (9H, s, ButSi), 3.48-3.56 (2H, m, 1-H2 or 3-H2), 3.64 (1H, dd, J 10 and 5.5 Hz, 1-H or 3-H), 3.68 (1H, dd, J 10 and 5 Hz, 1-H or 3-H), 3.86 (1H, quintet, J 5.5 Hz, 2-H), 4.56 (2H, s, —OCH2Ph) and 7.27-7.35 (5H, m, —Ph). the mixture was washed with H2O (2×100 mL) dried (MgSO4) concentrated

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 1 L beaker were weighed 222 g (1.0 mol) of 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane prepared in 1-2, 250 ml of ethanol, and 400 ml of distilled water, and the whole was adjusted to pH 2 with phosphoric acid. With introducing nitrogen thereinto, the solution was heated to 70° C. After 1.5 hours of the reaction, the solution was adjusted to pH 7.0 with sodium hydroxide. The resulting salt was subjected to adsorption treatment with an adsorbent “KYOWAAD 1000” (manufactured by Kyowa Hakko Kogyo Co., Ltd.) and then subjected to solvent removal to obtain 3-benzyloxy-1,2-propanediol. After 1.5 hours of the reaction subjected to solvent removal

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

Procedure: Into a suspension of water (1055 g) and sodium periodate (406 g) was dropped 3-benzyloxy-1,2-propanediol (366 g, 2.0 mol) at 20 to 25° C. over a period of 21 hours, and the mixture was stirred for 2 hours. Ethyl acetate (495 ml) was added, and the mixture was filtrated and washed. The aqueous layer was extracted with ethyl acetate (825 ml) again, and the organic layers were combined, and washed with a 10% sodium thiosulfate aqueous solution (363 g). The organic layer was treated with phosphoric acid to regulate pH to around 7, then, washed twice with 5% saline (660 g) and dehydrated over anhydrous magnesium sulfate (100 g). Magnesium sulfate was filtrated off, and hydroquinone (1.3 g) was added, the solvent was distilled off, to obtain a title compound (259 g, yield 85.9%). the mixture was filtrated washed The aqueous layer was extracted with ethyl acetate (825 ml) again washed with a 10% sodium thiosulfate aqueous solution (363 g) The organic layer was treated with phosphoric acid washed twice with 5% saline (660 g) Magnesium sulfate was filtrated off hydroquinone (1.3 g) was added the solvent was distilled off