Sodium borohydride → 5-chloro-4-(4-ethylbenzyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenol

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Reaction Steps

To a solution of 27 (100 mg, 0.125 mmol) in anhydrous THF (2 mL) under an argon blanket was added sodium borohydride (23.7 mg, 0.627 mmol). The resulting mixture was stirred for 2 hours, after which it was quenched with MeOH (1 mL) and AcOH (0.5 mL), followed by partitioning between water and EtOAc. The organic phase was dried over Na2SO4, filtered, and evaporated. The residue was loaded onto a preparatory TLC plate and eluted with 15% EtOAc in petroleum ether to give 28 (92 mg, 92% yield). 1H NMR (300 MHz, CDCl3) δ 8.64 (s, 1H), 7.15-7.35 (m, 16H), 7.07-7.14 (m, 3H), 6.91-6.99 (m, 7H), 4.78-4.82 (m, 3H), 4.62 (d, J=12.0 Hz, 1H), 4.31-4.48 (m, 4H), 4.15 (dd, J=4.2, 13.2 Hz, 1H), 3.81-4.03 (m, 7H), 3.74 (d, J=10.2 Hz, 1H), 3.63 (dd, J=2.3, 10.2 Hz, 1H), 2.53 (q, J=7.5 Hz), 1.66 (t, broad, J=5.4 Hz, 1H, OH?), 1.16 (t, J=7.5 Hz, 3H). LC/MS m/z 822 (M+Na).

Provenance & Evidence