Reacción #6107

ord-a168521407ce43298f3e0fd66fa637a9

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
COc1cc(S)cc(OC)c1OC
3,4,5-trimethoxybenzenethiol
N#[C][Hg][C]#N
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2
N#[C][Hg][C]#N
Hg(CN)2
→
COc1cc(S[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc(OC)c1OC
expected product
Rendimiento 28.0%
COc1cc(S[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc(OC)c1OC
3,4,5-trimethoxyphenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Rendimiento 28.0%

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
COc1cc(S)cc(OC)c1OC
3,4,5-trimethoxybenzenethiol
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 11.35 g (57.10-3 mol) of 3,4,5-trimethoxybenzenethiol, 14.32 g (57.10-3 mol) of mercuric cyanide, Hg(CN)2, and 22.15 g (62.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 7.52 g (yield: 28%) of the expected product are obtained.

Fuente

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