Pyridine → HCID 90357861, compound

Participants

Reaction Steps

To a solution of diethyl(((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate (0.40 g, 0.64 mmol, 1.0 equiv) in dry acetonitrile (23.5 mL) was added pyridine (0.6 mL, 7.36 mmol, 11.5 equiv) at 0° C. under argon atmosphere. Then, anhydrous TMSBr (1.65 mL, 10.2 mmol, 16.0 equiv) dissolved in 16.5 mL of dry acetonitrile was added dropwise at −5 to 0° C. The resulting mixture was stirred for 10 minutes. The resulting reaction mixture was allowed to warm to room temperature 4 hours and then the volatiles were removed in vacuo (bath temperature <15° C.). To the residue was added ice-cold water (10 mL), and the organic material was extracted into DCM (2×10 mL). The organic layer was then dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo (bath temperature <15° C.) to obtain (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonic acid (0.45 g) as a pale green solid. This material was directly taken forward to the next step without purification. ESI (M+1) 570.0; calc for C30H36NO8P 569.2.

Provenance & Evidence