Tributylstannane → HCID 86701269, compound

Participants

Reaction Steps

To a solution of (3S,6S,7R,8R)-3-(tert-butoxycarbonylamino)-8-(2-iodoethyl)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (30 mg, 0.057 mmol) in benzene (1.5 mL) was added Bu3SnH (27 mg, 0.091 mmol) and AIBN (1 mg) at room temperature (about 22° C.), and the reaction solution was heated to reflux. After 1 h, the solution was cooled to room temperature. The solvent was removed under vacuum and the residue was purified via column chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound (20 mg, 88%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 5.44-5.19 (m, 2H), 5.03 (dd, J=13.0, 6.9 Hz, 1H), 4.91-4.73 (m, 2H), 3.70-3.52 (m, 1H), 2.68-2.52 (m, 1H), 2.45 (ddd, J=19.2, 12.0, 6.2 Hz, 1H), 1.71-1.56 (m, 2H), 1.45 (s, J=9.2 Hz, 9H), 1.26 (d, J=6.2 Hz, 3H), 1.20 (d, J=7.0 Hz, 6H), 0.86 (t, J=7.4 Hz, 3H); ESIMS m/z 424 ([M+Na]+).

Provenance & Evidence