(Diethylamino)sulfur trifluoride → HCID 59013461, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1S,3′R,4′S,5′S,6′R)-5-chloro-6-(4-ethylbenzyl)-6′-(hydroxymethyl)-2,3,3′,4′,5′,6′-hexahydrospiro[indene-1,2′-pyran]-3′,4′,5′-triol (10 mg, 0.024 mmol) in CH2Cl2 (1 mL), was added DAST (9 μL, 0.072 mmol) at −78° C. The mixture was stirred for 30 min at −78° C., then allowed to warm to room temperature and stirred for another 3 h. The reaction was quenched by aqueous saturated NaHCO3. The organic layer was separated, dried with Na2SO4 and concentrated in vacuo. The resulting residue was purified by preparative HPLC to give 4 mg (40%) of title compound as a colorless solid. 1H NMR (CD3OD, 300 MHz): δ 7.24 (s, 1H), 7.19 (s, 1H), 7.08 (m, 4H), 4.63 (d, J=3.3 Hz, 1H), 4.47 (d, J=3 Hz, 1H), 4.04 (m, 2H), 3.59-3.38 (m, 4H), 2.93 (t, J=7.2 Hz, 2H), 2.58 (q, J=7.8 Hz, 2H), 2.54 (dt, J=13.5, 7.8 Hz, 1H), 2.08 (dt, J=13.5, 7.8 Hz, 1H), 1.19 (t, J=7.8 Hz, 3H).

Provenance & Evidence