Potassium Carbonate → HCID 21970483, compound

Participants

Reaction Steps

To a solution of 22 (4.40 g, 12.1 mmol) in 120 mL of methanol is added K2CO3 (5.97 g, 36.2 mmol). The reaction mixture is stirred at room temperature for 1.5 h and then neutralized with amberlite resin, filtered, concentrated and purified by flash chromatography (5% methanol/CH2Cl2) to yield 3.10 g (91%, 2 steps) of phenyl 2-azido-2,6-dideoxy-1-thio-L-galactopyranoside (23) as a 2.5:1 (α:β) mixture of anomers: Rf 0.10 (25% EtOAc/petroleum ether); 1H NMR (CDCl3, 270 MHz) mixture of anomers, δ 7.61-7.27 (m, 10H), 5.61 (d, J=5.3 Hz, 1H, H-1α), 4.50 (q, J=6.6 Hz, 1H, H-5α), 4.42 (d, J=9.9 Hz, 1H, H-1β), 4.11 (dd, J=10.1, 5.4 Hz, 2H, H-3α,β), 3.88-3.85 (m, 3H), 3.73 (br s, 1H), 3.63 (q, J=6.3 Hz, 1H, H-5β), 3.59-3.40 (m, 1H), 2.81 (br s, 1H, OH), 2.47 (br s, 1H, OH), 2.23 (br s, 1H, OH), 1.72 (br s, 1H, OH), 1.37 (d, J=6.3 Hz, 3H, H-6β), 1.30 (d, J=6.6 Hz, 3H, H-6α).

Provenance & Evidence