Reacción #2460194

ord-8a72d63c92ec4b51b8d91305a34d3727

Ecuación de reacción

CC(=O)c1ccccc1O
1-(2-hydroxyphenyl)ethanone
CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C(C)=O
expected product
Rendimiento 13.5%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C(C)=O
2-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
Rendimiento 13.5%

Reactantes

CC(=O)c1ccccc1O
1-(2-hydroxyphenyl)ethanone
CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide

Reactivos

[Cl-].[Cl-].[Zn+2]
zinc chloride
[Ag+].c1c[n-]cn1
silver imidazolate

Disolventes

CC#N
acetonitrile
ClCCl
methylene chloride

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroIf the procedure described in Preparation LXXXIII

Procedimiento

If the procedure described in Preparation LXXXIII is followed starting from 3.45 g (25.3.10-3 mol) of 1-(2-hydroxyphenyl)ethanone, 6 g (16.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 3 g (17.10-3 mol) of silver imidazolate and 4.6 g (33.7.10-3 mol) of zinc chloride in 90 ml of methylene chloride and 30 ml of acetonitrile, 0.92 g (yield: 13.5%) of the expected product is obtained after purification by chromatography on silica gel using a toluene/ethyl acetate mixture (6/1 v/v) as the eluent, and crystallization from ether.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05101048uspto-grants-1992_03