Reacción #6092

ord-6e155a0fcdfe4261a9d6e2ec6bcd8028

Ecuación de reacción

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-])c1ccc(S)cc1
4-nitrobenzenethiol
N#[C][Hg][C]#N
Hg(CN)2
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc([N+](=O)[O-])cc2)SC[C@H]1OC(C)=O
expected product
Rendimiento 66.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc([N+](=O)[O-])cc2)SC[C@H]1OC(C)=O
4-nitrophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Rendimiento 66.0%

Reactantes

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-])c1ccc(S)cc1
4-nitrobenzenethiol
—
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroIf the procedure described in Preparation I

Procedimiento

If the procedure described in Preparation I is followed starting from 6 g (38.10-3 mol) of 4-nitrobenzenethiol, 10.7 g (42.10-3 mol) of mercuric cyanide, Hg(CN)2, and 15.1 g (42.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 10.8 g (yield: 66%) of the expected product are obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05246961uspto-grants-1993_09