4-(2-Fluoroethoxy)benzoyl chloride → 4-Fluoro-3-(4-(2-fluoroethyloxy)phenylmethyl)-1-(beta-D-glucopyranosyl)indole

Participants

Reaction Steps

4-Fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 2-(3) and 4-(2-fluoroethyloxy)benzoyl chloride were treated in a manner similar to Example 2-(4), (5), (6) and (7) to give the titled compound as a colorless powder. APCI-Mass m/Z 467 (M+NH4). 1H-NMR (DMSO-d6) δ 3.15-3.41 (m, 4H), 3.65 (m, 2H), 4.01 (s, 2H), 4.12 (m, 1H), 4.22 (dd, J=4.7, 3.2 Hz, 1H), 4.53 (t, J=5.5 Hz, 1H), 4.63 (m, 1H), 4.78 (m, 1H), 5.09 (d, J=5.3 Hz, 1H), 5.16 (d, J=5.0 Hz, 1H), 5.21 (d, J=5.9 Hz, 1H), 5.36 (d, J=9.1 Hz, 1H), 6.74 (dd, J=11.4, 7.8 Hz, 1H), 6.87 (d, J=8.6 Hz, 2H), 7.06 (dt, J=8.1, 5.2 Hz, 1H), 7.18 (d, J=8.6 Hz, 2H), 7.20 (s, 1H), 7.35 (d, J=8.4 Hz, 1H).

Provenance & Evidence