D-ERYTHRONOLACTONE

D-ERYTHRONOLACTONE is white to light yellow crystal powde

Iso-ascorbic acid (17.6g, 0.1mol) was dissolved in 250ml of water and cooling to 0 ~ 6°C . Anhydrous sodium carbonate powder (21.2g, 0.2mol) was added portionwise reaction flask. After completion of the addition, stirring was continued while adding 30percent hydrogen peroxide (22mL), the internal temperature was increased from 6 to 19°C , stirring was continued in an ice bath for 5 minutes, the internal temperature rose to 27°C . The reaction solution was heated with stirring to 42°C 30 minutes. Zinc powder (1.0g, 0.015mol) was added to the reaction mixture was quenched with an excess of hydrogen peroxide, potassium iodide starch test paper showed negative. The reaction solution was adjusted with 6N hydrochloric acid to pH 1.0. Concentrated under reduced pressure at 50°C to a small volume to precipitate a white solid. With ethyl acetate (150mlx3) extraction. The organic phase was concentrated to 200ml (10 ~ 15vol); cooling to 15 ~ 25°C , stirring for 5 to 8 hours; (a lot of white solid precipitated) was filtered, dried to give 8.26g (3R, 4R) -3, 4- two hydroxy-dihydro-furan -2 (3H) - one, a yield of 70percentThe vitamin C (17.6g, 0 . 1mol) dissolved in a solvent (250 ml) in, cooling to 0 °C then adding sodium carbonate (21.2g, 0 . 2mol), and then adds volume percentage concentration is 30percent aqueous solution of hydrogen peroxide (46 ml, 0 . 45mmol), heating to 42 °C stirring reaction after 30 min, then cooling to -10 ° C adding manganese dioxide after (28.7g, 0 . 33mol), then heating to 60 °C, reaction is carried out under stirring, until the starch potassium iodide paper test until the residual hydrogen peroxide-free, end of the reaction, the reaction solution;The solvent is distilled water, its consumption according to the vitamin C: solvent is 1mol: 2.5L calculated in proportion to the;The above-mentioned the reaction heterobasidion vitamin C, sodium carbonate, volume percentage concentration is 30percent of the amount of the aqueous solution of hydrogen peroxide and manganese dioxide, ratio calculation process, that is, vitamin C: sodium carbonate: volume percentage concentration is 30percent aqueous solution of hydrogen peroxide: manganese dioxide as 1:2: 0.0045 : 3.3;Filtering the resulting reaction solution, the filtrate obtained by the used for quality percentage concentration of 36percent hydrochloric acid aqueous solution to adjust pH to 1, then the control pressure is 2×10To a solution of d-erythronolactone (2.00 g, 16.9 mmol) in dichloromethane (80 ml) held at -78 C under argon were successively added pyridine (6.85 ml, 84.7 mmol, 5.0 equiv) and a solution of trifluoromethanesulfonic anhydride (7.60 ml, 45.7 mmol, 2.7 equiv) in dichloromethane (20 ml). After 15 min of stirring at -78 C, the reaction mixture was slowly warmed to -25 C over a period of 3.5 h. The reaction solution was then poured into cold diethyl ether (200 ml). The precipitate was filtered, and the filtrate was evaporated under reduced pressure at 0 C. The resulting residue was rapidly purified by filtration on silica gel (Et2O) to afford compound 8 (3.62 g, 92%) as a yellow oil, which was directly used in the next step. To a solution of compound 8 (3.62 g, 15.6 mmol) in DMF (70 ml) at -30 C under argon was added dropwise p-methoxybenzylamine (3.06 ml, 23.4 mmol, 1.5 equiv). The reaction mixture was stirred for 1 h at -30 C before being diluted with ethyl acetate (60 ml) and water (60 ml). The layers were separated, and the aqueous phase was extracted with ethyl acetate (2×60 ml). The combined organic extracts were dried over magnesium sulfate and evaporated to dryness. The resulting residue was purified by flash chromatography on silica gel (Et2O/petroleum ether 2:1) to give the p-methoxybenzylaziridine-gamma-lactone 6 (1.53 g, 45%) as an amorphous solid.

A chiral synthon used for the synthesis of certain natural products such as the leukotrienes