Acetic Acid → (3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-(2-phenylmethoxyethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol

Participants

Reaction Steps

A solution of 129 (4.5 g, 9.4 mmol) in methanol (40 mL) was treated with potassium carbonate (260 mg, 2 mmol) for 3 hours at room temperature, then neutralized by the addition of acetic acid (0.5 mL). Volatiles were distilled out to give a residue, which was solidified from ethyl acetate. The solids were washed with ethyl acetate (3×20 mL) to give 130 as a light yellow solid (2.58 g, 80%). (ES, m/z) [M+H]+ 355.0; 1H NMR (300 MHz, D2O) δ 7.27-7.37 (m, 5H), 6.17 (d, J=6.3 Hz, 1H), 4.48 (s, 2H), 4.34-4.37 (m, 1H), 4.03-4.07 (m, 1H), 3.88-3.91 (m, 1H), 3.58-3.67 (m, 2H), 3.31-3.55 (m, 5H).

Provenance & Evidence