Vanillic Acid → HCID 67607156, compound

Participants

Reaction Steps

Vanillic acid having a benzyl-protected hydroxyl group at the 4 position and 2,3,4,6-tetrabenzyl glucose having benzyl-protected hydroxyl groups at positions other than the 1 position (Sigma-Aldrich) were condensed in a DMF solvent (at a reaction temperature of 60° C.) using the following condensing agents: 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI, Kokusaikagaku Co., Ltd.), 4-dimethylaminopyridine (DMAP, Tokyo Kasei Kogyo), and triethylamine (Et3N, Wako Pure Chemical Industries, Ltd.). The obtained condensate was a mixture comprising a anomer and β anomer at a ratio of 1:2. The condensate was purified using an open column (at different concentration ratios of hexane:ethyl acetate=6:1 and 5:1). A unreacted starting material was removed. The yield was found to be 84%: Molecular MS [M+Na]+ m/z 803.14, 1H NMR (300 MHz, CDCl3): δ7.60 (1H, dd, H-6), 7.59 (1H, d, H-2), 7.45-7.26 (60H, m, H-benzylic CH2), 6.90 (1H, d, H-5), 6.55 (1H, d, H-Glc1α, J=3.21), 5.84 (1H, d, H-Glc1β, J=7.65), 5.25 (10H, s, H-benzylic CH2), 4.96-3.56 (94H, m, CH3, H-Glc).

Provenance & Evidence