5-sulfanylpentan-1-ol

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

Procedure: 1.26 g (5.94 mmoles) of 4(RS)-t-butyldimethylsilyloxy-2,3-epoxy cyclopentanone and 804 mg (6.0 mmoles) of 5-hydroxy-1-pentanethiol were dissolved in 10 ml of methanol, and 606 mg (6 mmoles) of triethylamine was added. After the reaction was carried out for 10 minutes, the solvent was evaporated to give 2.1 g of a crude product. The crude product was subjected to dry column chromatography and developed with hexane/ethyl acetate (7/3) to give 710 mg (2.16 mmoles; yield 31%) of 4-t-butyldimethylsilyloxy-2-(6-hydroxyhexylthio)-2-cyclopentenone. the solvent was evaporated to give 2.1 g of a crude product to dry column chromatography

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

Procedure: 1.4 g of sodium hydride at 50% in oil and 6 g of bromo N-butyl-N-methyl acetamide of Step A of Preparation B of Example 78 were added to a solution of 3.36 g of the product of Step A in 45 ml of tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred for 2 hours at ambient temperature and poured into an ammonium chloride solution and extracted with ethyl acetate. The extracts were washed and evaporated to dryness under reduced pressure. The 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8) to obtain 5.27 g of the expected product. extracted with ethyl acetate The extracts were washed evaporated to dryness under reduced pressure The 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8)

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

Procedure: 1.4 g of sodium hydride at 50% in oil and 6 g of bromo N-butyl-N-methyl acetamide of Step A of Preparation B of Example 78 were added to a solution of 3.36 g of the product of Step A in 45 ml of tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred for 2 hours at ambient temperature and poured into an ammonium chloride solution and extracted with ethyl acetate. The extracts were washed and evaporated to dryness under reduced pressure. The 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8) to obtain 5.27 g of the expected product. extracted with ethyl acetate The extracts were washed evaporated to dryness under reduced pressure The 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8)

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

Procedure: 1.4 g of sodium hydride at 50% in oil and 6 g of bromo N-butyl-N-methyl acetamide of Step A of Preparation B of Example 78 were added to a solution of 3.36 g of the product of Step A in 45 ml of tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred for 2 hours at ambient temperature and poured into an ammonium chloride solution and extracted with ethyl acetate. The extracts were washed and evaporated to dryness under reduced pressure. The 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8) to obtain 5.27 g of the expected product. extracted with ethyl acetate The extracts were washed evaporated to dryness under reduced pressure The 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8)

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

Procedure: 1.26 g (5.94 mmoles) of 4(RS)-t-butyldimethylsilyloxy-2,3-epoxy cyclopentanone and 804 mg (6.0 mmoles) of 5-hydroxy-1-pentanethiol were dissolved in 10 ml of methanol, and 606 mg (6 mmoles) of triethylamine was added. After the reaction was carried out for 10 minutes, the solvent was evaporated to give 2.1 g of a crude product. The crude product was subjected to dry column chromatography and developed with hexane/ethyl acetate (7/3) to give 710 mg (2.16 mmoles; yield 31%) of 4-t-butyldimethylsilyloxy-2-(6-hydroxyhexylthio)-2-cyclopentenone. the solvent was evaporated to give 2.1 g of a crude product to dry column chromatography

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

Procedure: 1.26 g (5.94 mmoles) of 4(RS)-t-butyldimethylsilyloxy-2,3-epoxy cyclopentanone and 804 mg (6.0 mmoles) of 5-hydroxy-1-pentanethiol were dissolved in 10 ml of methanol, and 606 mg (6 mmoles) of triethylamine was added. After the reaction was carried out for 10 minutes, the solvent was evaporated to give 2.1 g of a crude product. The crude product was subjected to dry column chromatography and developed with hexane/ethyl acetate (7/3) to give 710 mg (2.16 mmoles; yield 31%) of 4-t-butyldimethylsilyloxy-2-(6-hydroxyhexylthio)-2-cyclopentenone. the solvent was evaporated to give 2.1 g of a crude product to dry column chromatography

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

Procedure: 1.4 g of sodium hydride at 50% in oil and 6 g of bromo N-butyl-N-methyl acetamide of Step A of Preparation B of Example 78 were added to a solution of 3.36 g of the product of Step A in 45 ml of tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred for 2 hours at ambient temperature and poured into an ammonium chloride solution and extracted with ethyl acetate. The extracts were washed and evaporated to dryness under reduced pressure. The 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8) to obtain 5.27 g of the expected product. extracted with ethyl acetate The extracts were washed evaporated to dryness under reduced pressure The 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8)

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

Procedure: 1.4 g of sodium hydride at 50% in oil and 6 g of bromo N-butyl-N-methyl acetamide of Step A of Preparation B of Example 78 were added to a solution of 3.36 g of the product of Step A in 45 ml of tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred for 2 hours at ambient temperature and poured into an ammonium chloride solution and extracted with ethyl acetate. The extracts were washed and evaporated to dryness under reduced pressure. The 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8) to obtain 5.27 g of the expected product. extracted with ethyl acetate The extracts were washed evaporated to dryness under reduced pressure The 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8)

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

Procedure: 1.26 g (5.94 mmoles) of 4(RS)-t-butyldimethylsilyloxy-2,3-epoxy cyclopentanone and 804 mg (6.0 mmoles) of 5-hydroxy-1-pentanethiol were dissolved in 10 ml of methanol, and 606 mg (6 mmoles) of triethylamine was added. After the reaction was carried out for 10 minutes, the solvent was evaporated to give 2.1 g of a crude product. The crude product was subjected to dry column chromatography and developed with hexane/ethyl acetate (7/3) to give 710 mg (2.16 mmoles; yield 31%) of 4-t-butyldimethylsilyloxy-2-(6-hydroxyhexylthio)-2-cyclopentenone. the solvent was evaporated to give 2.1 g of a crude product to dry column chromatography