m-Chloroperbenzoic acid → ((2'S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-7-chloro-6-(4-ethylbenzyl)-3',4',5',6'-tetrahydrospiro[chroman-4,2'-pyran]-2-yl)methanol

Participants

Reaction Steps

To a solution of 34 (70 mg, 86 μmol) in anhydrous DCM (1 mL) was added 3-chlorobenzoperoxoic acid (23 mg, 104 μmol, 1.2 equiv). The reaction was stirred overnight, directly loaded onto a preparatory TLC plate, and eluted with 15% EtOAc in petroleum ether to give 39 (17 mg, 24% yield), a single diastereomer. 1H NMR (300 MHz, CDCl3) δ 7.14-7.32 (m, 18H), 6.98 (d, J=8.1 Hz, 2H), 6.96 (s, 1H), 6.90 (d, J=8.1 Hz, 2H), 6.79-6.83 (m, 2H), 4.85 (d, J=10.8 Hz, 1H), 4.80 (s, 2H), 4.58 (d, J=10.8 Hz, 1H), 4.57 (d, J=12.0 Hz, 1H), 4.45 (d, J=12.0 Hz, 1H), 4.37 (d, J=10.8 Hz, 1H), 4.07-4.15 (m, 1H), 4.05 (d, J=15.6 Hz, 1H), 3.61-3.91 (m, 10H), 2.49 (q, J=7.5 Hz), 2.08-2.35 (m, 3H), 1.12 (t, J=7.5 Hz, 3H). LCMS m/z 826 (M+H), 848 (M+Na).

Provenance & Evidence