Reaktion #6112

ord-5695140c336e4ddc99bfce8ba1baa852

Reaktionsgleichung

N#Cc1ccc(-c2ccc(S)cc2)cc1
4-(4-mercaptophenyl)benzonitrile
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
N#[C][Hg][C]#N
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(-c3ccc(C#N)cc3)cc2)SC[C@H]1OC(C)=O
expected product
Ausbeute 10.2%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(-c3ccc(C#N)cc3)cc2)SC[C@H]1OC(C)=O
4-(4-cyanophenyl)phenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Ausbeute 10.2%

Edukte

N#Cc1ccc(-c2ccc(S)cc2)cc1
4-(4-mercaptophenyl)benzonitrile
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
N#[C][Hg][C]#N
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 2.3 g (10.9.10-3 mol) of 4-(4-mercaptophenyl)benzonitrile, 4.26 g (11.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 2.75 g (10.9.10-3 mol) of mercuric cyanide (Hg(CN)2), 0.540 g (yield: 10%) of the expected product is obtained after purification by flash chromatography using methylene chloride as the eluent.

Quelle

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