Reacción #6114

ord-21012e4031214f1599ceb78ee6f4b6dc

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
FC(F)(F)c1cc(S)cc(C(F)(F)F)c1
3,5-bis(trifluoromethyl)benzenethiol
N#[C][Hg][C]#N
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2
N#[C][Hg][C]#N
Hg(CN)2
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cc(C(F)(F)F)cc(C(F)(F)F)c2)SC[C@H]1OC(C)=O
expected product
Rendimiento 35.7%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cc(C(F)(F)F)cc(C(F)(F)F)c2)SC[C@H]1OC(C)=O
3,5-bis(trifluoromethyl)phenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Rendimiento 35.7%

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
FC(F)(F)c1cc(S)cc(C(F)(F)F)c1
3,5-bis(trifluoromethyl)benzenethiol
N#[C][Hg][C]#N
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2
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 1.6 g (6.5.10-3 mol) of 3,5-bis(trifluoromethyl)benzenethiol, 1.64 g (6.5.10-3 mol) of mercuric cyanide, Hg(CN)2, and 2.54 g (7.5.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1.2 g (yield: 35.7%) of the expected product are obtained. M.p.=201° C.

Fuente

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