Tetrahydrofuran → (1R,2S,3R,4R,5S,6R)-4-(4-chloro-2-(4-ethylbenzyl)phenoxy)-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetraol

Participants

Reaction Steps

14 mL of THF and methanol (1:1) was added to the flask containing the (1S,2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohexanol (28, 55 mg, 0.070 mmol). 55 mg of Pd/C (10%) was added in one portion to the reaction mixture. The mixture was degassed five times with H2 and the resulting suspension was stirred under an atmosphere of H2 for 3 h at ambient temperature. The reaction mixture was filtered and concentrated, and the residue was purified by preparative LC-MS to obtain 25 mg of (1R,2S,3R,4R,5S,6R)-4-(4-chloro-2-(4-ethylbenzyl)phenoxy)-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetraol (29). 1H-NMR (D2O): δ 7.22˜7.2 (1H, d, J=9.2 Hz), 7.17˜7.11 (4H, q), 7.08˜7.06 (1H, dd), 6.92˜6.91 (1H, d, J=3.2 Hz), 4.11˜4.08 (1H, t J=9.2 Hz), 4.01 (2H, s), 3.92˜3.91 (2H, m), 3.69˜3.665 (1H, dd, J=10.8, 8.8 Hz), 3.46˜3.39 (2H, m), 3.35˜3.30 (1H, m), 2.66˜2.58 (2H, q), 1.52˜1.46 (1H, tt), 1.24˜1.19 (3H, t).

Provenance & Evidence