反应 #632059

ord-4e2d8febaa8748299846dc6ab3e05441

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(OCCF)cc1
4-(2-fluoroethyloxy)benzoyl chloride
OC[C@H]1O[C@@H](n2cc(Cc3ccc(OCCF)cc3)c3c(Cl)cccc32)[C@H](O)[C@@H](O)[C@@H]1O
titled compound
OC[C@H]1O[C@@H](n2cc(Cc3ccc(OCCF)cc3)c3c(Cl)cccc32)[C@H](O)[C@@H](O)[C@@H]1O
4-Chloro-3-(4-(2-Fluoroethyloxy)phenylmethyl)-1-(β-D-glucopyranosyl)indole

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-(2-fluoroethyloxy)benzoyl chloride were treated in a manner similar to Example 3 to give the titled compound as a colorless powder. APCI-Mass m/Z 466/468 (M+H). 1H-NMR (DMSO-d6) δ 3.24 (td, J=8.8, 5.7 Hz, 1H), 3.38-3.47 (m, 3H), 3.62-3.69 (m, 2H), 4.14-4.16 (m, 1H), 4.20 (s, 2H), 4.20-4.22 (m, 1H), 4.53 (t, J=5.5 Hz, 1H), 4.66-4.67 (m, 1H), 4.76-4.77 (m, 1H), 5.09 (d, J=5.31 Hz, 1H), 5.15 (d, J=5.0 Hz, 1H), 5.21 (d, J=5.8 Hz, 1H), 5.39 (d, J=9.0 Hz, 1H), 6.87 (d, J=8.7 Hz, 2H), 7.02 (d, J=7.5 Hz, 1H), 7.09 (t, J=7.9 Hz, 1H), 7.15 (d, J=8.5 Hz, 2H), 7.22 (s, 1H), 7.53 (d, J=8.2 Hz, 1H).

来源

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