Novel compounds
A compound and pharmaceutical technology, applied in the field of drug application, can solve the problem of less data
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Embodiment 1
[0221]
[0222] (2R,3S,4R,5S,6R)-2-(Hydroxymethyl)-6-((R)-1-(2-methyl-4-(5-(trifluoromethyl)pyrazine-2 -yl)phenyl)ethyl)tetrahydro-2H-pyran-3,4,5-triol
[0223]
[0224] (4-bromo-2-methylphenyl)((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl )tetrahydro-2H-pyran-2-yl)methanone
[0225] At 0°C, to (R)-(4-bromo-2-methylphenyl)((2R,3S,4S,5R,6R)-3,4,5-tri(benzyloxy)-6 -((Benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (2g, 2.76mmol) and pyridine (660mg, 8.35mmol) in DCM (20mL) was added Dess-Martin Reagent (Dess-Martin periodinane) (2.34 g, 5.52 mmol). The reaction mixture was stirred at 25°C for 2 hours. Upon completion, the reaction was quenched with water (20 mL), extracted with DCM (20 mL×3), the organic phases were combined, washed with brine (20 mL), washed over MgSO 4 Drying and concentration in vacuo gave a residue (2g) as a yellow oil which was used in the next step without further purification. ESI-MS[M+Na] + (C 42 h 41 BrO 6 Na + ) calcu...
Embodiment 2
[0244] (2R,3S,4R,5S,6R)-2-(Hydroxymethyl)-6-((R)-1-(2-methyl-4-(4-(trifluoromethyl)pyridine-2- yl)phenyl)ethyl)tetrahydro-2H-pyran-3,4,5-triol
[0245]
[0246] 2-(3-Methyl-4-(1-((2R,3R,4R,5R,6R)-3,4,5-tri(benzyloxy)-6-((benzyloxy)methyl Base) tetrahydro-2H-pyran-2-yl) ethyl) phenyl) -4- (trifluoromethyl) pyridine
[0247] To 4,4,5,5-tetramethyl-2-(3-methyl-4-(1-((2R,3R,4R,5R,6R)-3,4,5-tri(benzyloxy Base)-6-((Benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethyl)phenyl)-1,3,2-dioxaborolane (800mg , 1.041mmol) in 1,4-dioxane (8mL) and water (2.0mL) were added 2-chloro-4-(trifluoromethyl)pyridine (189mg, 1.041mmol), tetrakis(triphenylphosphine ) palladium (0) (120mg, 0.104mmol), Cs 2 CO 3 (678 mg, 2.081 mmol). The resulting solution was stirred at 80°C for 1.5 hours. The reaction mixture was cooled to room temperature, quenched with water (10 mL), extracted with ethyl acetate (10 mL x 3), washed over Na 2 SO 4 Dry and filter. The filtrate was concentrated to give a residu...
Embodiment 3
[0258]
[0259] (2R,3S,4R,5S,6R)-2-(Hydroxymethyl)-6-((R)-1-(2-(trifluoromethyl)-4-(5-(trifluoromethyl) Pyrazin-2-yl)phenyl)ethyl)tetrahydro-2H-pyran-3,4,5-triol
[0260]
[0261] (4-bromo-2-(trifluoromethyl)phenyl)((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy Base) methyl) tetrahydro-2H-pyran-2-yl) ketone
[0262] At 0°C, to (S)-(4-bromo-2-(trifluoromethyl)phenyl)((2R,3S,4S,5R,6R)-3,4,5-tri(benzyloxy yl)-6-((Benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (5.45 g, 7.01 mmol) in DCM (50 mL) was added pyridine (1.700 mL, 21.02 mmol ), Dess-Martin reagent (5.94g, 14.02mmol). The reaction mixture was then stirred at 0 °C for 2 hours. A sample was taken from the reaction mixture and diluted with MeOH, and analyzed by LCMS, which indicated that the reaction was complete. The reaction mixture was washed with 10% Na 2 S 2 o 3 (aqueous solution) (50mL) / saturated NaHCO 3 (aq) (50 mL) was quenched and then extracted with DCM (10 mLx3). The combined organic lay...
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