Ethanol → HCID 67930784, compound

Participants

Reaction Steps

A solution of 1,6-anhydro-2,4-di-O-benzyl-β-D-allopyranose (Example 20) (1 g, 2.9 mmol), sodium hydride (60%, 200 mg, 5 mmol), methyl iodide (excess) and tetrabutylammonium iodide (trace) in tetrahydrofuran was stirred overnight at room temperature. Ethanol was added to destroy excess sodium hydride and the solution evaporated to near dryness. The residue was taken up in dichloromethane and washed with water and brine. The organic phase was dried (Na2SO4) and evaporated, and the residue was chromatographed on silica gel (hexane/ethyl acetate, 1:1) to give the title compound as a colourless syrup (800 mg, 77%), [α]D -53.6°; 13C-nmr data: 128.2, 128.0, 127.9 (aromatic), 100.5 (C-1), 74.6 and 74.1 (C-2 and C-4), 73.6 (OCH2Ph), 73.5 and 73.1 (C-3 and C-5), 72.2 (OCH2Ph), 64.8 (C-6), and 56.8 (OCH3).

Provenance & Evidence