Réaction #6117

ord-d94fb37375fe483b836d9caf4ed1219f

Équation de réaction

N#Cc1ccc(S)c(C#N)c1
3-cyano-4-mercaptobenzonitrile
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#N)cc2C#N)SC[C@H]1OC(C)=O
expected product
Rendement 47.9%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc(C#N)cc2C#N)SC[C@H]1OC(C)=O
2,4-dicyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Rendement 47.9%

Réactifs

—
IV
N#Cc1ccc(S)c(C#N)c1
3-cyano-4-mercaptobenzonitrile
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

Réactifs

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

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

If the procedure described in Preparation IV is followed starting from 1.6 g (9.73.10-3 mol) of 3-cyano-4-mercaptobenzonitrile, 4.07 g (11.45.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 0.84 g (10.10-3 mol) of zinc oxide (ZnO), 2.08 g (yield: 47%) of the expected product are obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05246961uspto-grants-1993_09