Water → HCID 67930806, compound

Participants

Reaction Steps

1,6-Anhydro-4-O-benzyl-2-O-methyl-β-D-allopyranose (0.135 g) (see Example 29) was dissolved in dimethylsulphoxide (0.5 ml) and stirred with powdered potassium hydroxide (0.118 g). Methyl iodide (0.568 g) was added in two portions, and the reaction mixture was left overnight at room temperature. Water (10 ml) was added and the mixture was extracted with chloroform (3×10 ml). The combined extracts were washed with brine, filtered through Whatman 1PS paper, and evaporated to a red oil. This was subjected to preparative t.l.c. on silica gel eluted with ethyl acetate/hexane, 1:1, to yield the title compound as a colourless syrup (0.073 g); 1H-nmr data: 7.2-7.5 (m, Ph), 5.6 (d, H-1), 4.8 (m, PhCH2O), 4.55 (m, H-5), 3.3-3.7 (m, H-2,3,4,6,6'), and 3.40 and 3.57 (s, OMe).

Provenance & Evidence