Reaktion #6103

ord-9c45a27a7f934ba4b93e4d1e32569393

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
O=[N+]([O-])c1ccccc1S
2-nitrobenzenethiol
N#[C][Hg][C]#N
Hg(CN)2
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2[N+](=O)[O-])SC[C@H]1OC(C)=O
expected product
Ausbeute 48.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2[N+](=O)[O-])SC[C@H]1OC(C)=O
2-nitrophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Ausbeute 48.0%

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
O=[N+]([O-])c1ccccc1S
2-nitrobenzenethiol
—
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 6 g (38.7.10-3 mol) of 2-nitrobenzenethiol, 10.75 g (42.5.10-3 mol) of mercuric cyanide, Hg(CN)2, and 15.12 g (42.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 8 g (yield: 48%) of the expected product are obtained.

Quelle

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