Reacción #6131

ord-14c101d07d4f4ec98d6975cff8caa0ec

Ecuación de reacción

C[O-].[Na+]
sodium methylate
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc([N+](=O)[O-])cc1
4-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
→
O=[N+]([O-])c1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1
expected product
Rendimiento 81.1%
O=[N+]([O-])c1ccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1
4-nitrophenyl 5-thio-β-D-xylopyranoside
Rendimiento 81.1%

Reactantes

C[O-].[Na+]
sodium methylate
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccc([N+](=O)[O-])cc1
4-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
—
solution

Reactivos

Ninguno

Disolventes

CO
methanol
CO
methanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONAfter complete solubilization (2 h), the reaction mixture is neutralized by the addition of Amberlite® IR 120 H+ resin
  2. 2
    Filtraciónfiltered

Procedimiento

0.2 ml of a solution of sodium methylate in methanol (8% w/v of Na) is added under an inert atmosphere to a suspension of 1.1 g (2.6.10-3 mol) of 4-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside in 30 ml of methanol. After complete solubilization (2 h), the reaction mixture is neutralized by the addition of Amberlite® IR 120 H+ resin and then filtered. 620 mg (yield: 79%) of the expected product are obtained after evaporation to dryness and lyophilization.

Fuente

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