HCID 11793622, compound → HCID 44414214, compound

Participants

Reaction Steps

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-propene (4.15 g, 11.14 mmol) in CH3OH (50 mL) was added NaOCH3 (0.56 mL, 2.2 mmol, 4.0 M in CH3OH). After stirring at rt for 2 hr, the reaction mixture was neutralized using Dowex 50W (acidic form). The resin was filtered off and the filtrate was concentrated to give the title compound. 1H NMR (DMSO-d6) δ 2.09 (m, 1H), 2.49 (m, 1H), 2.88 (t, J=8.9, 1H), 2.98-3.07 (m, 3H), 3.11 (m, 1H), 3.39 (dd, J=11.4, 4.7, 1H), 3.60 (d, J=11.6, 1H), 4.99 (dd, J=10.3, 0.9, 1H), 5.06 (d, J=17.2, 1H), 5.90 (m, 1H).

Provenance & Evidence