5-Ethylthiophene-2-carbonyl chloride → 4-Chloro-3-(5-ethylthiophen-2-yl-methyl)-1-(beta-D-glucopyranosyl)indole

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Reaction Steps

4-Chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 1-(3) and 5-ethylthiophen-2-carbonyl chloride were treated in a manner similar to Example 2-(4), (5), (6) and (7) to give the titled compound as a pink powder. APCI-Mass m/Z 455/457 (M+NH4). 1H-NMR (DMSO-d6) δ 1.17 (t, J=7.4 Hz, 3H), 2.71 (q, J=7.4 Hz, 2H), 3.15-3.43 (m, 4H), 3.67 (m, 2H), 4.36 (s, 2H), 4.54 (t, J=5.5 Hz, 1H), 5.10 (d, J=5.3 Hz, 1H), 5.16 (d, J=5.0 Hz, 1H), 5.20 (d, J=5.9 Hz, 1H), 5.40 (d, J=9.1 Hz, 1H), 6.62 (m, 2H), 7.04 (m, 1H), 7.11 (t, J=7.9 Hz, 1H), 7.38 (s, 1H), 7.54 (d, J=8.2 Hz, 1H).

Provenance & Evidence