反应 #632054

ord-9fa43d0559b84051ad818f79273ec5d9

反应方程式

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
O=C(Cl)c1ccc(OCCF)cc1
4-(2-fluoroethyloxy)benzoyl chloride
OC[C@H]1O[C@@H](n2cc(Cc3ccc(OCCF)cc3)c3c(F)cccc32)[C@H](O)[C@@H](O)[C@@H]1O
titled compound
OC[C@H]1O[C@@H](n2cc(Cc3ccc(OCCF)cc3)c3c(F)cccc32)[C@H](O)[C@@H](O)[C@@H]1O
4-Fluoro-3-(4-(2-fluoroethyloxy)phenylmethyl)-1-(β-D-gluco-pyranosyl)indole

反应条件

详细条件
See reaction.notes.procedure_details.

实验过程

4-Fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 2-(3) and 4-(2-fluoroethyloxy)benzoyl chloride were treated in a manner similar to Example 2-(4), (5), (6) and (7) to give the titled compound as a colorless powder. APCI-Mass m/Z 467 (M+NH4). 1H-NMR (DMSO-d6) δ 3.15-3.41 (m, 4H), 3.65 (m, 2H), 4.01 (s, 2H), 4.12 (m, 1H), 4.22 (dd, J=4.7, 3.2 Hz, 1H), 4.53 (t, J=5.5 Hz, 1H), 4.63 (m, 1H), 4.78 (m, 1H), 5.09 (d, J=5.3 Hz, 1H), 5.16 (d, J=5.0 Hz, 1H), 5.21 (d, J=5.9 Hz, 1H), 5.36 (d, J=9.1 Hz, 1H), 6.74 (dd, J=11.4, 7.8 Hz, 1H), 6.87 (d, J=8.6 Hz, 2H), 7.06 (dt, J=8.1, 5.2 Hz, 1H), 7.18 (d, J=8.6 Hz, 2H), 7.20 (s, 1H), 7.35 (d, J=8.4 Hz, 1H).

来源

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