Pyridine → HCID 86621844, compound

Participants

Reaction Conditions

Reaction Steps

2-((2S,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-2-methoxytetrahydro-2H-pyran-2-yl)ethanol (8) (0.46 g, 0.77 mmol) was dissolved in CH2Cl2 (2 mL). Pyridine (0.31 mL, 3.85 mmol) and TsCl (0.29 g, 1.54 mmol) were added and the reaction mixture was heated at 50° C. for 18 h. Additional TsCl (0.05 g, 0.26 mmol) was then added and the reaction mixture was heated at 50° C. for another 4 hours. The mixture was concentrated onto celite and chromatographed over SiO2, (ISCO system, 0-40% EtOAc/hexanes) to provide an oil (0.317 g, 55%). 1H NMR (300 MHz, CDCl3) δ ppm: 7.66 (d, J=8.4 Hz, 2H), 7.14-7.32 (m, 22H), 4.77-4.89 (m, 4H), 4.46-4.57 (m, 4H), 3.86-4.07 (m, 1H), 3.48-3.64 (m, 4H), 3.31 (d, J=9.3 Hz, 1H), 3.17 (s, 3H), 2.36 (s, 3H), 2.13 (t, J=8.1 Hz, 1H). LC/MS tR=3.37 min, calcd for C44H48O9S: 752.3, found 775.2 (M+Na)+.

Provenance & Evidence