Acetic Acid → HCID 54236291, compound

Participants

Reaction Steps

To a solution of (-)-(2R,4R)-4-(2-benzoxy-1-hydroxyethyl)-2-(t-butyldiphenylsilyloxy-methyl)-dioxolane (2.52 g, 5.0 mmole) in methanol (40 ml) was added a 0.078 M solution of sodium methoxide (7.3 ml) in methanol. The mixture stirred at room temperature for two hours. The mixture was neutralized with acetic acid and concentrated. The residue was then portioned between ethyl acetate and water, and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with a saturated NaHCO3 solution and then water, and then dried, evaporated, and purified by column chromatography over silica gel to yield 6 (1.9 g, 95%) as colorless oil: [α]25D-2° (C 0.25, MeOH); 1H NMR (DMSO-d6) δ 1.00 (s, 9H, t-Bu), 3.40-3.52 (m, 3H, CH2OH and CHOH), 3.64 (d, J=3.7 Hx, 2H, CH2O TBDPS), 3.82-3.95 (m, 3H, 4.5-H), 4.49 (t, J-5.3 Hz, 1H, pri OH, D2O exchangeable), 4.82 (d, J=5.1 Hz, 1H, sec OH, D2O exchangeable), 5.01 (t, J-3.7 Hz, 1H, 2-H), 7.36-7.71 (m, 1OH, Ar--H); Anal. Calcd for C22H33H30O5Si: C, 65.63; H, 7.53. Found: C, 65.72; H, 7.52.

Provenance & Evidence