Réaction #632048

ord-16872815f7c3481c8b4b8aada449b53a

Équation de réaction

CC(=O)OC[C@H]1O[C@@H](n2ccc3c(Cl)cccc32)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
4-Chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole
O=C(Cl)c1ccc(Cl)cc1
4-chlorobenzoyl chloride
CC(=O)OC[C@H]1O[C@@H](n2cc(C(=O)c3ccc(Cl)cc3)c3c(Cl)cccc32)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indol-3-yl 4-chlorophenyl ketone

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

4-Chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole obtained in Example 1-(3) and 4-chlorobenzoyl chloride were treated in a manner similar to Example 2-(4) to give 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indol-3-yl 4-chlorophenyl ketone as a colorless powder. APCI-Mass m/Z 620/622 (M+H). 1H-NMR (DMSO-d6) δ 1.69 (s, 3H), 1.97 (s, 3H), 1.98 (s, 3H), 2.04 (s, 3H), 4.11 (br-d, J=4.2 Hz, 2H), 4.30 (m, 1H), 5.28 (t, J=9.8 Hz, 1H), 5.53 (t, J=9.6 Hz, 1H), 5.73 (t, J=9.4 Hz, 1H), 6.34 (d, J=9.2 Hz, 1H), 7.29 (d, J=7.7 Hz, 1H), 7.38 (t, J=8.0 Hz, 1H), 7.62 (d, J=8.5 Hz, 2H), 7.80 (d, J=8.5 Hz, 1H), 7.82 (d, J=8.5 Hz, 2H), 8.18 (s, 1H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07935674B2uspto-grants-2011_05