1-Benzofuran-5-carbonyl chloride → benzo[b]furan-5-yl 4-chloro-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indol-3-yl ketone

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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 benzo[b]furan-5-carbonyl chloride were treated in a manner similar to Example 2-(4) to give benzo[b]furan-5-yl 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indol-3-yl ketone as a colorless powder. APCI-Mass m/Z 626/628 (M+H). 1H-NMR (DMSO-d6) δ 1.74 (s, 3H), 1.97 (s, 3H), 1.98 (s, 3H), 2.03 (s, 3H), 4.10-4.11 (m, 2H), 4.30 (dt, J=9.9, 4.2 Hz, 1H), 5.27 (t, J=9.9 Hz, 1H), 5.54 (t, J=9.6 Hz, 1H), 5.74 (t, J=9.3 Hz, 1H), 6.34 (d, J=9.0 Hz, 1H), 7.06 (d, J=1.3 Hz, 1H), 7.28 (d, J=7.5 Hz, 1H), 7.37 (t, J=8.0 Hz, 1H), 7.75 (d, J=8.7 Hz, 1H), 7.81 (d, J=8.3 Hz, 1H), 7.85 (dd, J=8.6, 1.7 Hz, 1H), 8.12 (d, J=1.4 Hz, 1H), 8.13 (s, 2H).

Provenance & Evidence