Potassium Carbonate → HCID 178456833, compound

Participants

Reaction Steps

(5R,6S,7R)-5-(acetoxymethyl)-2-(allylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (0.281 g, 0.73 mmol) was dissolved in anhydrous MeOH. Solid K2CO3 was added to the solution until it was basic, and the reaction was stirred at room temperature (1.5 h). The reaction was filtered and then concentrated in vacuo. The crude material was purified via flash column chromatography (DCM:MeOH, 5:2) providing (5R,6S,7R)-2-(allylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (31) (0.048 g, 18% yield). 1H NMR: (500 MHz, methanol-d4) δ 3.50 (dd, 1H, J=5.5, 8.9 Hz), 3.6-3.7 (m, 2H), 3.81 (d, 1H, J=10.7 Hz), 3.87-3.95 (m, 3H), 4.09 (t, 1H, J=6.2 Hz), 5.15 (d, 1H, J=10.3 Hz), 5.25 (d, 1H, J=17.2 Hz), 5.88-5.96 (m, 1H), 6.36 (d, 1H, J=6.4 Hz). 13C NMR (125 MHz, methanol-d4) δ: 39.23, 61.80, 69.52, 73.52, 74.51, 75.39, 90.67, 161.87, 165.33.

Provenance & Evidence