4-Ethylbenzoyl chloride → 3-(4-ethylphenylmethyl)-4-methyl-1-(beta-D-glucopyranosyl)indole

Participants

Reaction Steps

The above 4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyl)indole and 4-ethylbenzoyl chloride were treated in a manner similar to Example 3 to give the titled compound, 3-(4-ethylphenylmethyl)-4-methyl-1-(β-D-glucopyranosyl)-indole as a colorless powder. APCI-Mass m/Z 412 (M+H). 1H-NMR (DMSO-d6) δ 1.15 (t, J=−1.6 Hz, 3H), 2.41 (s, 3H), 2.56 (q, J=7.5 Hz, 2H), 3.23 (td, J=8.9, 5.2 Hz, 1H), 3.37-3.47 (m, 3H), 3.64-3.69 (m, 2H), 4.16 (s, 2H), 4.51 (t, J=5.3 Hz, 1H), 5.06 (d, J=5.1 Hz, 1H), 5.13-5.15 (m, 2H), 5.34 (d, J=9.0 Hz, 1H), 6.70 (d, J=7.1 Hz, 1H), 6.97 (t, J=7.7 Hz, 1H), 7.07-7.12 (m, 5H), 7.34 (d, J=8.3 Hz, 1H).

Provenance & Evidence