ethylsulfanyl(trimethyl)silane

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

Procedure: A mixture of galactose pentaacetate (38.00 g, 97.43 mmol), (ethylthio)trimethylsilane (19.60 g, 146.15 mmol) and trimethylsilyl trifluoromethanesulfonate (23.60 g, 106.20 mmol) in CH2Cl2 (150 ml) was stirred overnight at room temperature. The reaction mixture was diluted with CH2Cl2 (150 ml) and washed with 1M Na2CO3 solution (300 ml), water (300 ml), dried over MgSO4 and concentrated. The residue was crystallised from hexane/diisopropyl ether 1:1 (v/v) to give ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (34.00 g, 89%). washed with 1M Na2CO3 solution (300 ml), water (300 ml) dried over MgSO4 concentrated The residue was crystallised from hexane/diisopropyl ether 1:1 (v/v)

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

Procedure: A mixture of galactose pentaacetate (38.00 g, 97.43 mmol), (ethylthio)trimethylsilane (19.60 g, 146.15 mmol) and trimethylsilyl trifluoromethanesulfonate (23.60 g, 106.20 mmol) in CH2Cl2 (150 ml) was stirred overnight at room temperature. The reaction mixture was diluted with CH2Cl2 (150 ml) and washed with 1M Na2CO3 solution (300 ml), water (300 ml), dried over MgSO4 and concentrated. The residue was crystallised from hexane/di-isopropyl ether 1:1 (v/v) to give ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (34.00 g, 89%). washed with 1M Na2CO3 solution (300 ml), water (300 ml) dried over MgSO4 concentrated The residue was crystallised from hexane/di-isopropyl ether 1:1 (v/v)