Toluene → (3R,4S,5R,6R)-3,4,5-Tris-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-tetrahydro-pyran-2-on

Participants

Reaction Steps

At −7° C., TMSCl (71 mL) was added into a solution of (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one (14.2 g) and N-methylmorpholine (80 mL) in dry THF (120 mL), and then the mixture was slowly warmed up to room temperature and stirred overnight. At 10° C., toluene (160 mL) and H2O (300 mL) were poured into the mixture, and then the organic phase was washed with H2O (120 mL), 1M HCl (150 mL×4) and brine (120 mL). The organic phase was dried over Na2SO4, and concentrated to obtain the crude product, then the crude product was purified by silica-gel column chromatography (PE/EA=10/1) to obtain 30 g of (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one.

Provenance & Evidence