4-Ethoxybenzoyl Chloride → 4,6-dichloro-3-(4-ethoxyphenylmethyl)-1-(beta-D-glucopyranosyl)-indole

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Reaction Steps

The above 4,6-dichloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole and 4-ethoxybenzoyl chloride were treated in a manner similar to Example 3 to give the titled compound, 4,6-dichloro-3-(4-ethoxyphenylmethyl)-1-(β-D-glucopyranosyl)-indole as a colorless powder. APCI-Mass m/Z 499/501 (M+NH4). 1H-NMR (DMSO-d6) δ 1.29 (t, J=7.0 Hz, 3H), 3.15-3.52 (m, 4H), 3.58 (m, 1H), 3.67 (m, 1H), 3.97 (q, J=6.9 Hz, 2H), 4.17 (s, 2H), 4.54 (t, J=5.6 Hz, 1H), 5.10 (d, J=5.3 Hz, 1H), 5.15 (d, J=5.1 Hz, 1H), 5.21 (d, J=5.8 Hz, 1H), 5.45 (d, J=9.0 Hz, 1H), 6.81 (d, J=8.5 Hz, 2H), 7.11 (m, 3H), 7.26 (s, 1H), 7.71 (d, J=1.1 Hz, 1H).

Provenance & Evidence