(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-one → HCID 68794922, compound

Participants

Reaction Steps

To a solution of (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one 5 (1.10 g, 2.04 mmol) and 1-bromo-4-chloro-5-(4-ethylbenzyl)-2-methoxybenzene 22 (0.60 g, 1.77 mmol) in anhydrous THF (20 mL) at −78° C. was added a solution of n-BuLi (0.78 mL, 1.94 mmol, 2.5 M). The mixture was stirred for 1 h, warmed to ambient temperature, quenched with 10% sodium carbonate (100 mL), and extracted with ethyl acetate (2×50 mL). The organic phase was dried with anhydrous MgSO4, filtered, and evaporated to dryness. The residue was purified by silica gel column chromatography using 15-25% ethyl acetate in petroleum ether to give 23 (0.91 g, 64%). LC/MS m/z 822 (M+Na), 782 (M−OH).

Provenance & Evidence