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

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Reaction Steps

A solution of (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-2-(2-fluoroethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (29 g, 74 mmol) in methanol (200 mL) was treated with potassium carbonate (1 g, 7 mmol) overnight at room temperature. The solids were collected by filtration and washed with dichloromethane (3×50 mL) to afford compound 67 as a white solid (18 g, 92%). (ES, m/z) [M+H]+ 266.9; 1H NMR (300 MHz, D2O) δ 6.21-6.23 (d, J=6.3 Hz, 1H), 4.55-4.59 (m, 1H), 4.40-4.44 (m, 1H), 4.10-4.14 (t, J=5.7 Hz, 1H), 3.95-3.98 (t, J=5.4 Hz, 1H), 3.70-3.75 (m, 1H), 3.40-3.62 (m, 5H).

Provenance & Evidence