(2ξ,5R)-1,5-Anhydro-3,4-dideoxy-5-C-(2,5-difluorophenyl)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-D-glycero-pentitol

1G (8.9 g, 28.6 mmol) was dissolved in dry methyl t-butyl ether (90 ml), dry toluene (9 ml) was added thereto, the temperature was lowered to -10°C, and a solution of borane dimethyl sulfide in tetrahydrofuran (2 mol/l, 35.9 ml)was added dropwise, followed by reaction at 0°C for 3.5 hours. Water (4 ml) was added slowly, a sodium hydroxidesolution (1 mol/l, 89 ml) was added dropwise, followed by stirring for 15 min, and sodium perborate (13.2 g, 85.8 mmol)was added in batches, followed by stirring at room temperature overnight. The reaction solution was allowed to settleand be partitioned, and the aqueous phase was extracted with methyl t-butyl ether (50 ml32). The organic phases werecombined, washed with a saturated sodium chloride solution (20 ml32), dried by addition of anhydrous sodium sulfatethereto, filtered, concentrated, followed by addition of toluene (50 ml), and dissolved by heating to 90°C. n-hexane (200ml) was added dropwise to the reaction solution to precipitate a white solid, followed by filtration. The filter cake waswashed with n-hexane (30 ml32), and the solvent was removed by concentrating, to obtain a white solid powder 1H(7.9 g, yield 84percent).MS m/z (ESI): 274.1 [M-55].1G (8.9 g, 28.6 mmol) was dissolved in dry methyl tertiary butyl ether (90 mL)Dry toluene (9 mL) was added and the temperature was reduced to -10 ° C, A solution of borane dimethyl sulfide tetrahydrofuran (2 mol / L, 35.9 mL) was added dropwise and reacted at 0 ° C for 3.5 hours.Water (4 mL) was slowly added, and sodium hydroxide solution (1 mol / L, 89 mL) was added dropwise. The mixture was stirred for 15 minutes. Sodium perborate (13.2 g, 85.8 mmol) was added portionwise and stirred at room temperature overnight.The organic phase was washed with anhydrous sodium sulfate, filtered, and the organic phase was washed with anhydrous sodium sulfate (20 mL x 2)(50 mL) was added, dissolved by heating to 90 ° C, and n-hexane (200 mL) was added dropwise to the reaction solution to precipitate a white solid which was filtered, N-hexane (30 mL x 2), and the solvent was concentrated to give a white solid, 1H (7.9 g, 84percent yield).1G (8.9 g, 28.6 mmol) was dissolved in dry methyl tertiary butyl ether (90 mL), dried toluene (9 mL) was added and the temperature was lowered to -10 ° C. Add dropwise in to borane dimethyl sulfide tetrahydrofuran solution2 mol / L, 35.9 mL) and reacted at 0 ° C for 3.5 hours. Water (4 mL) was slowly added, and sodium hydroxide solution (1 mol / L, 89 mL) was added dropwise. The mixture was stirred for 15 minutes. Sodium perborate (13.2 g, 85.8 mmol) was added portionwise and stirred at room temperature overnight. The organic phase was washed with anhydrous sodium sulfate, filtered, concentrated, and the organic phase was washed with anhydrous sodium sulfate. The organic phase was washed with anhydrous sodium sulfate. Toluene (50 mL) was added and the mixture was dissolved in 90 ° C and n-hexane (200 mL) was added dropwise to the reaction solution to precipitate a white solid which was filtered and filtered with n-hexane (30 mL x 2). The solvent was concentrated to give a white solid (7.9 g, yield 84percent).1G (8.9 g, 28.6 mmol) was dissolved in dry methyl tertiary butyl ether (90 mL) Dry toluene (9 mL) was added and the temperature was reduced to -10 °C, Added dropwise Borane dimethyl sulfide tetrahydrofuran solution (2 mol / L, 35.9 mL), The reaction was carried out at 0 ° C for 3.5 hours. Water (4 mL) was slowly added, and sodium hydroxide solution (1 mol / L, 89 mL) was added dropwise, stirred for 15 minutes, Sodium perborate (13.2 g, 85.8 mmol) was added portionwise and stirred at room temperature overnight.The organic phase was washed with anhydrous sodium sulfate, filtered and concentrated, and the organic phase was washed with anhydrous sodium sulfate (20 mL x 2) (50 mL) was added and heated to 90 °C to dissolve. N-Hexane (200 mL) was added dropwise to the reaction solution to precipitate a white solid, filtered and n-hexane (30 mL x 2). The filter cake was concentrated and the solvent was concentrated to give a white solid powder 1H (7.9 g, yield 84percent).The 1G (8.9g, 28.6mm0l) Was dissolved in dry methyl tertiary butyl ether (9 mL) Add dry toluene (9 mL), The temperature drops to -10 ° C, A solution of borane dimethyl sulfide tetrahydrofuran (2 mol / L, 35.9 mL) was added dropwise, Reaction at 0 ° C for 3.5 hours. Slowly add water (4 mL), A solution of sodium hydroxide (1 ml / L, 89 mL) was added dropwise, After stirring for 5 minutes, sodium perborate (13.2 g, 85.8 mmol) was added in portions, Stir at room temperature for 25 nights. The layers were separated and the aqueous phase was extracted with methyl t-butyl ether (50 mL x 2) The organic phase was combined, washed with saturated sodium chloride solution (20 mL x 2) The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, Add toluene (50 mL) and heat to 90 ° C1G (8.9 g, 28.6 mmol) was dissolved in dry methyl tertiary butyl ether (90 mL)Dry toluene (9 mL) was added and the temperature was reduced to -10 ° C, Added dropwiseBorane dimethyl sulfideTetrahydrofuran solution(2 mol / L, 35.9 mL) and reacted at 0 ° C for 3.5 hours.Slowly add water (4 mL), A solution of sodium hydroxide (1 mol / L, 89 mL) was added dropwise, stirred for 15 minutes, Joined in batchesSodium perborate(13.2 g, 85.8 mmol), Stir overnight at room temperature.Allowed to separate, and the aqueous phase was extracted with methyl tert.butyl ether (50mL × 2), the combined organic phases, the organic phase was washed with saturated sodium chloride solution (20mL × 2), dried over anhydrous sodium sulfate, filtered, and concentrated Toluene (200 mL) was added dropwise to the reaction solution, and a white solid was precipitated, filtered and n-hexane (30 mL x 2) was used to wash the filter cake, and the solvent was concentrated to remove the solvent. To the residue was added to the residue, To give white solid powder 1H (7.9 g, yield 84percent)1G (8.9 g, 28.6 mmol) was dissolved in dry methyl tert-butyl ether (90 mL)Dry toluene (9 mL) was added, The temperature drops to -10 ° C, A solution of borane dimethyl ether sulfide in tetrahydrofuran was added dropwiseliquid(2 mol / L, 35.9 mL)The reaction was carried out at 0 ° C for 3.5 hours.Slowly add water (4 mL), A solution of sodium hydroxide (1 mol / L, 89 mL) was added dropwise, Stir for 15 minutes, Sodium perborate (13.2 g, 85.8 mmol) was added in portions, Stir overnight at room temperature.Static liquid separation, The aqueous phase was extracted with methyl tert-butyl ether (50 mL x 2)Combined organic phase, The organic phase was washed with saturated sodium chloride solution (20 mL x 2)Dried over anhydrous sodium sulfate, filter, concentrate, Toluene (50 mL) was added to the residue, Heated to 90 ° C dissolved, N-hexane (200 mL) was added dropwise to the reaction solution, Precipitation of white solid, filter, N-hexane (30 mL x 2)The solvent was removed by concentration, To give white solid powder 1H (7.9 g, yield 84percent).Tert-butyl (2R, 3S)-2-(2, 5-difluorophenyl)-3, 4-dihydro-2H-pyran-3-ylcarbamate (2.81g, 9.04 mmol) was dissolved in 50 mL of tetrahydrofuran and cooled to -10°C. Borane-dimethyl sulfide complex (2.26 mL, 22.6 mmol) was added dropwise, stirred at low temperature for 2 hours and then warmed to 15°C. N-Boc- (2R, 3S) -2- (2, 5- difluorophenyl) -3, 4-dihydro -2H- pyran-3-amine (compound 6) (1.55g, 5mmol) was added to 20mL of methyl tert-butyl ether, began stirring until completely dissolved, then the reaction solution was cooled to -10 deg.] C, was slowly added boron trifluoride borane complex solution (2mol / L, 5mL, 10mmol), stirred for 3 hours after slow addition of water (1.8g, 100mmol), maintaining a temperature of 0-10 deg.] C the reaction was stirred for 3 hours.Was then added aqueous sodium bicarbonate (5percent, 20mL) and sodium hydroxide solution (1percent, 10mL).Then to the reaction mixture was slowly added solid sodium borate (1.17g, 15mmol).The reaction system was then stirred for 10 hours at room temperature continued.The reaction solution was extracted with ethyl acetate three times using 30mL, extracted with sodium bicarbonate solution, washed with a saturated sodium chloride solution twice, the resultant wash liquor was concentrated to dryness, the residue was purified by silica gel column chromatography (eluent : ethyl acetate, n-hexane) to give a white solid (1.2g, purity 98.2percent, yield: 72.9percent).

Molecular Weight:329.34
XLogP3:2.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:329.14386448
Monoisotopic Mass:329.14386448
Topological Polar Surface Area:67.8
Heavy Atom Count:23
Complexity:415
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes