Pyridine → HCID 90357162, compound

Participants

Reaction Steps

To a solution of (((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate (0.6 g, 0.89 mmol, 1.0 equiv) in dry acetonitrile (60 mL) was added pyridine (1.1 mL, 10.2 mmol, 11.5 equiv) at 0° C. under argon atmosphere. TMSBr (2.5 mL, 17.7 mmol, 20 equiv) dissolved in dry acetonitrile (25 mL) was added dropwise to the reaction mixture at 0° C. which was stirred for 10 minutes and then warmed to room temperature and stirred for 3 hours. The volatiles were removed in vacuo (bath temperature <15° C.) to give an oil. Ice cold water (20 mL) was added, and the organic material was extracted into DCM (2×80 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo (bath temp <15° C.) to give ((((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonic acid as a pale green solid (0.50 g). The material thus obtained was used without further purification. ESI (M+1) m/z: 619.0; calc for C35H39O8P 618.2.

Provenance & Evidence