(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-methylsulfanyloxane-3,4,5-triol

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

Procedure: A mixture of methyl 1-thio-β-D-galactopyranoside (25) 5 g, 28 mmol), chloro t-butyldiphenylsilane (5.85 g, 21 mmol) and DMAP (2.63 g, 21 mmol) in dry 1,2-dichloroethane (130 mL) was left to stir at reflux for 2.5 h. The reaction mixture was cooled to room temperature, diluted with dichloromethane (200 mL) and washed with saturated sodium chloride solution (2×250 mL). The organic phase was dried over MgSO4 and subsequently evaporated to dryness to give methyl 6-O-(t-butyldiphenylsilyl)-1-thio-β-D-galactopyranoside (26) (7.5 g, 81%) as a colorless oil. was left at reflux for 2.5 h washed with saturated sodium chloride solution (2×250 mL) The organic phase was dried over MgSO4 subsequently evaporated to dryness

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

Procedure: A mixture of methyl 1-thio-β-D-galactopyranoside (25) 5 g, 28 mmol), chloro t-butyldiphenylsilane (5.85 g, 21 mmol) and DMAP (2.63 g, 21 mmol) in dry 1,2-dichloroethane (130 mL) was left to stir at reflux for 2.5 h. The reaction mixture was cooled to room temperature, diluted with dichloromethane (200 mL) and washed with saturated sodium chloride solution (2×250 mL). The organic phase was dried over MgSO4 and subsequently evaporated to dryness to give methyl 6-O-(t-butyldiphenylsilyl)-1-thio-β-D-galactopyranoside (26) (7.5 g, 81%) as a colorless oil. was left at reflux for 2.5 h washed with saturated sodium chloride solution (2×250 mL) The organic phase was dried over MgSO4 subsequently evaporated to dryness

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

Procedure: A mixture of methyl 1-thio-β-D-galactopyranoside (25) 5 g, 28 mmol), chloro t-butyldiphenylsilane (5.85 g, 21 mmol) and DMAP (2.63 g, 21 mmol) in dry 1,2-dichloroethane (130 mL) was left to stir at reflux for 2.5 h. The reaction mixture was cooled to room temperature, diluted with dichloromethane (200 mL) and washed with saturated sodium chloride solution (2×250 mL). The organic phase was dried over MgSO4 and subsequently evaporated to dryness to give methyl 6-O-(t-butyldiphenylsilyl)-1-thio-β-D-galactopyranoside (26) (7.5 g, 81%) as a colorless oil. was left at reflux for 2.5 h washed with saturated sodium chloride solution (2×250 mL) The organic phase was dried over MgSO4 subsequently evaporated to dryness