bis(trimethylsilyl) sulfate

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

Procedure: A mixture of 13 g 1,2,3-tris(10-[tetrahydropyranyloxy]decyloxy)propane, 1 g bis(trimethylsilyl)sulphate and 250 ml methanol is stirred at room temperature for 2 hours. The reaction mixture is evaporated down. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (1/1 v/v) as eluent and recrystallisation from acetonitrile to yield 7.1 g of 1,2,3-tris(10-hydroxydecyloxy)propane. The reaction mixture is evaporated down The residue is purified by column chromatography on silica gel recrystallisation from acetonitrile

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

Procedure: A mixture of 13 g 1,2,3-tris(10-[tetrahydropyranyloxy]decyloxy)propane, 1 g bis(trimethylsilyl)sulphate and 250 ml methanol is stirred at room temperature for 2 hours. The reaction mixture is evaporated down. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (1/1 v/v) as eluent and recrystallisation from acetonitrile to yield 7.1 g of 1,2,3-tris(10-hydroxydecyloxy)propane. The reaction mixture is evaporated down The residue is purified by column chromatography on silica gel recrystallisation from acetonitrile

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

Procedure: A solution of 1.2 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 40 ml of methanol and 2 ml of diethyl ether was treated with a solution of 7.3 mg of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at room temperature for 2 hours and then treated with 0.2 ml of pyridine. Subseguently, the reaction mixture was concentrated and the residue was then taken up in 50 ml of dichloromethane, washed twice with water, dried over magnesium sulfate, filtered and again concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from methanol gave 0.5 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexanol. Subseguently, the reaction mixture was concentrated washed twice with water dried over magnesium sulfate filtered again concentrated The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1) Recrystallization from methanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3.0 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexanol, 1.1 ml of 3,4-dihydro-2H-pyran in 30 ml of dichloromethane was treated at 0° C. with a solution of 0.007 g of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at 0° C. for a further 30 minutes and then washed once with sodium carbonate solution and twice with water and subsequently dried over magnesium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from ethyl acetate at -20° C. gave 1.75 g of pure trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether. washed once with sodium carbonate solution and twice with water subsequently dried over magnesium sulfate filtered concentrated The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1) Recrystallization from ethyl acetate at -20° C.

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

Procedure: A solution of 1.2 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 40 ml of methanol and 2 ml of diethyl ether was treated with a solution of 7.3 mg of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at room temperature for 2 hours and then treated with 0.2 ml of pyridine. Subseguently, the reaction mixture was concentrated and the residue was then taken up in 50 ml of dichloromethane, washed twice with water, dried over magnesium sulfate, filtered and again concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from methanol gave 0.5 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexanol. Subseguently, the reaction mixture was concentrated washed twice with water dried over magnesium sulfate filtered again concentrated The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1) Recrystallization from methanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3.0 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexanol, 1.1 ml of 3,4-dihydro-2H-pyran in 30 ml of dichloromethane was treated at 0° C. with a solution of 0.007 g of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at 0° C. for a further 30 minutes and then washed once with sodium carbonate solution and twice with water and subsequently dried over magnesium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from ethyl acetate at -20° C. gave 1.75 g of pure trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether. washed once with sodium carbonate solution and twice with water subsequently dried over magnesium sulfate filtered concentrated The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1) Recrystallization from ethyl acetate at -20° C.

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

Procedure: A mixture consisting of 400.5 mg (1.20 mmoles) of 7-benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide, 0.69 g (4.3 mmoles) of N-trimethylsilylurethane and 20 mg of bis-(trimethylsilyl)-sulfate in 40 ml of dichloromethane was refluxed for 3/4 hours after which a clear solution was obtained. This was cooled in an ice-bath and bromination was carried out after the addition of 200 mg (2.04 mmoles) of amidosulfonic acid using 325.3 mg (1.83 mmoles) of N-bromosuccinimide as the brominating agent. The bromination took half an hour to obtain a 65% yield of trimethylsilyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxide. was refluxed for 3/4 hours after which a clear solution was obtained This was cooled in an ice-bath The bromination took half an hour

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

Procedure: A solution of 1.2 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 40 ml of methanol and 2 ml of diethyl ether was treated with a solution of 7.3 mg of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at room temperature for 2 hours and then treated with 0.2 ml of pyridine. Subsequently, the reaction mixture was concentrated and the residue was then taken up in 50 ml of dichloromethane, washed twice with water, dried over magnesium sulfate, filtered and again concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9;1). Recrystallization from methanol gave 0.5 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexanol. Subsequently, the reaction mixture was concentrated washed twice with water dried over magnesium sulfate filtered again concentrated The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9;1) Recrystallization from methanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3.0 g of trans-4-(4'-cyano-4biphenylyl)cyclohexanol. 1.1 ml of 3,4-dihydro-2H-pyran in 30 ml of dichloromethane was treated at 0° C. with a solution of 0.007 g of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at 0° C. for a further 30 minutes and then washed once with sodium carbonate solution and twice with water and subsequently dried over magnesium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9;1). Recrystallization from ethyl acetate at -20° C. gave 1.75 g of pure trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether. washed once with sodium carbonate solution and twice with water subsequently dried over magnesium sulfate filtered concentrated The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9;1) Recrystallization from ethyl acetate at -20° C.

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

Procedure: A mixture of 13 g 1,2,3-tris(10-[tetrahydropyranyloxy]decyloxy)propane, 1 g bis(trimethylsilyl)sulphate and 250 ml methanol is stirred at room temperature for 2 hours. The reaction mixture is evaporated down. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (1/1 v/v) as eluent and recrystallisation from acetonitrile to yield 7.1 g of 1,2,3-tris(10-hydroxydecyloxy)propane. The reaction mixture is evaporated down The residue is purified by column chromatography on silica gel recrystallisation from acetonitrile

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

Procedure: A solution of 1.2 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 40 ml of methanol and 2 ml of diethyl ether was treated with a solution of 7.3 mg of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at room temperature for 2 hours and then treated with 0.2 ml of pyridine. Subseguently, the reaction mixture was concentrated and the residue was then taken up in 50 ml of dichloromethane, washed twice with water, dried over magnesium sulfate, filtered and again concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from methanol gave 0.5 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexanol. Subseguently, the reaction mixture was concentrated washed twice with water dried over magnesium sulfate filtered again concentrated The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1) Recrystallization from methanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3.0 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexanol, 1.1 ml of 3,4-dihydro-2H-pyran in 30 ml of dichloromethane was treated at 0° C. with a solution of 0.007 g of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at 0° C. for a further 30 minutes and then washed once with sodium carbonate solution and twice with water and subsequently dried over magnesium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from ethyl acetate at -20° C. gave 1.75 g of pure trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether. washed once with sodium carbonate solution and twice with water subsequently dried over magnesium sulfate filtered concentrated The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1) Recrystallization from ethyl acetate at -20° C.