Reaction #632050

ord-96088ff4485742918b7d0be1aae3157d

Reaction equation

CC(=O)OC[C@H]1O[C@@H](n2ccc3c(F)cccc32)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

4-Fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole

4-ethoxybenzoyl chloride

→

CCOc1ccc(C(=O)c2cn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)c3cccc(F)c23)cc1

4-ethoxyphenyl 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyl)indol-3-yl ketone

Reactants

4-Fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole

4-ethoxybenzoyl chloride

Reagents

None

Conditions

Detailed conditions

See reaction.notes.procedure_details.

Procedure

4-Fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole obtained in Example 2-(3) and 4-ethoxybenzoyl chloride were treated in a manner similar to Example 2-(4) to give 4-ethoxyphenyl 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyl)indol-3-yl ketone as a colorless powder. APCI-Mass m/Z 614 (M+H). 1H-NMR (DMSO-d6) δ 1.38 (t, J=6.9 Hz, 3H), 1.68 (s, 3H), 1.97 (s, 3H), 1.98 (s, 3H), 2.04 (s, 3H), 4.11 (d, J=4.0 Hz, 2H), 4.16 (q, J=7.0 Hz, 2H), 4.28-4.31 (m, 1H), 5.30 (t, J=9.8 Hz, 1H), 5.54 (t, J=9.6 Hz, 1H), 5.76 (t, J=9.3 Hz, 1H), 6.34 (d, J=9.0 Hz, 1H), 7.01 (dd, J=10.6, 8.0 Hz, 1H), 7.07 (d, J=8.7 Hz, 2H), 7.36 (td, J=8.1, 4.9 Hz, 1H), 7.62 (d, J=8.3 Hz, 1H), 7.83 (d, J=8.8 Hz, 2H), 8.14 (s, 1H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07935674B2uspto-grants-2011_05