Reacción #6108

ord-86b0005ef8c14e33b6bf5c9a49e82eb2

Ecuación de reacción

O=[N+]([O-])c1cccc(S)c1
3-nitrobenzenethiol
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](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](Sc2cccc([N+](=O)[O-])c2)SC[C@H]1OC(C)=O
expected product
Rendimiento 27.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc([N+](=O)[O-])c2)SC[C@H]1OC(C)=O
3-nitrophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Rendimiento 27.0%

Reactantes

O=[N+]([O-])c1cccc(S)c1
3-nitrobenzenethiol
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](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide

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 10 g (64.5.10-3 mol) of 3-nitrobenzenethiol, 16.29 g (64.5.10-3 mol) of mercuric cyanide (Hg(CN)2) and 25.2 g (70.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 7.44 g (yield: 27%) of the expected product are obtained after purification by flash chromatography using a toluene/ethyl acetate mixture (9/1 v/v) as the eluent, followed by crystallization from ether.

Fuente

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