Triphenylphosphine → (1S,3'R,4'S,5'S,6'R)-6'-(aminomethyl)-5-chloro-6-(4-ethylbenzyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triol

Participants

Reaction Steps

To a solution of (1S,3′R,4′S,5′S,6′R)-6′-(azidomethyl)-5-chloro-6-(4-ethylbenzyl)-3′,4′,5′,6′-tetrahydro-3H-spiro[isobenzofuran-1,2′-pyran]-3′,4′,5′-triol (25 mg, 0.056 mmol) in 0.5 mL of THF/H2O (4:1), was added PPh3 (43 mg, 0.164 mmol). The solution was stirred at room temperature for 4.5 h. Then the volatiles were removed under reduced pressure using a rotary evaporator. The resulting residue was purified by preparative HPLC to give 14 mg of title compound. 1H NMR (CD3OD, 300 MHz) δ 7.39 (s, 1H), 7.23 (s, 1H), 7.10 (s, 4H), 5.16 (d, J=12.8 Hz, 1H), 5.10 (d, J=12.8 Hz, 1H), 4.13 (d, J=15.6 Hz, 1H), 4.05 (d, J=15.6 Hz, 1H), 4.02-3.94 (m, 1H), 3.75 (dd, J=4.1, 1.1 Hz, 2H), 3.34-3.32 (m, 2H□, 2.98-2.91 (m, 1H □, 2.60 (q, J=7.5 Hz, 2H), 1.20 (t, J=7.5 Hz, 3H); MS ESI (m/z) 420 (M+1)+, calc. 419.

Provenance & Evidence