反应 #632070

ord-87c693f0fd8241249151e54a44f4a876

反应方程式

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(F)cc1
4-fluorobenzoyl chloride
CC(=O)OC[C@H]1O[C@@H](n2cc(C(=O)c3ccc(F)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-fluorophenyl ketone

反应条件

详细条件
See reaction.notes.procedure_details.

实验过程

4-Chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole obtained in Example 1-(3) and 4-fluorobenzoyl 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-fluorophenyl ketone as a colorless powder. APCI-Mass m/Z 604/606 (M+H). 1H-NMR (DMSO-d6) δ 1.69 (s, 3H), 1.79 (s, 3H), 1.98 (s, 3H), 2.04 (s, 3H), 4.11 (d, J=3.9 Hz, 2H), 4.27-4.33 (m, 1H), 5.29 (t, J=9.8 Hz, 1H), 5.54 (t, J=9.6 Hz, 1H), 5.72 (t, J=9.4 Hz, 1H), 6.33 (d, J=9.0 Hz, 1H), 7.28 (d, J=7.3 Hz, 1H), 7.35-7.42 (m, 3H), 7.80 (d, J=8.3 Hz, 1H), 7.89 (dd, J=8.4, 5.7 Hz, 2H), 8.16 (s, 1H).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07935674B2uspto-grants-2011_05