Reaktion #6096

ord-6e968d420acc44f5a9c97e2954212c9c

Reaktionsgleichung

FC(F)(F)c1ccc(S)cc1
4trifluoromethylbenzenethiol
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C(F)(F)F)cc2)SC[C@H]1OC(C)=O
expected product
Ausbeute 48.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C(F)(F)F)cc2)SC[C@H]1OC(C)=O
4-trifluoromethylphenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Ausbeute 48.0%

Edukte

—
IV
FC(F)(F)c1ccc(S)cc1
4trifluoromethylbenzenethiol
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide

Reagenzien

[O-2].[Zn+2]
zinc oxide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

If the procedure described in Preparation IV is followed starting from 5.6 g (32.10-3 mol) of 4trifluoromethylbenzenethiol, 12.3 g (35.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 2.55 g (32.10-3 mol) of zinc oxide (ZnO), 7.4 g (yield: 48%) of the expected product are obtained after precipitation in ether.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246961uspto-grants-1993_09