Reaktion #6095

ord-0e5f513459a84d2786a08726e0e9d65d

Reaktionsgleichung

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
FC(F)(F)c1ccc(S)cc1
4-tri-fluoromethylbenzenethiol
N#[C][Hg][C]#N
Hg(CN)2
→
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 40.0%
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 40.0%

Edukte

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
FC(F)(F)c1ccc(S)cc1
4-tri-fluoromethylbenzenethiol
—
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeIf the procedure described in Preparation I

Vorschrift

If the procedure described in Preparation I is followed starting from 5.58 g (32.10-3 mol) of 4-tri-fluoromethylbenzenethiol, 8.87 g (35.10-3 mol) of mercuric cyanide, Hg(CN)2, and 12.3 g (35.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 6.2 g (yield: 40%) of the expected product are obtained.

Quelle

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