Reacción #2358565

Ecuación de reacción

D-glucose

3,4,5-tribenzyloxybenzoic acid

EDC.HCl

→

product

Rendimiento 9.4%

β-D-Glucopyranose Pentakis[3,4,5-tris(phenylmethoxy)-benzoate]

Rendimiento 9.4%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux overnight
3. 3
   OtroThe cooled reaction mixture
4. 4
   Extracciónwas then extracted with 1N HCl (3×), saturated NaHCO3 (2×), and brine (2×)
5. 5
   Secadothe organic layer was dried over MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe resulting residue was purified by column chromatography over silica gel (75:24:1 CH2Cl2:toluene:ethyl acetate)

Procedimiento

A mixture of 1.17 mmol of D-glucose, 8.57 mmol of 3,4,5-tribenzyloxybenzoic acid, 10.68 mmol of EDC.HCl and 9.84 mmol of DMAP was suspended in 130 mL of CH2Cl2 and was heated at reflux overnight. The cooled reaction mixture was then extracted with 1N HCl (3×), saturated NaHCO3 (2×), and brine (2×), the organic layer was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by column chromatography over silica gel (75:24:1 CH2Cl2:toluene:ethyl acetate) to provide 0.253 g (9%) of product. 1H NMR (CDCl3, 400 MHz) δ 7.45-7.15 (m, 85H), 6.21 (d, J=8.0 Hz, 1H), 6.05 (t, J=10.0 Hz, 1H), 5.84 (dd, J=10.0, 8.0 Hz, 1H), 5.73 (t, J=10.0 Hz, 1H), 5.14-4.92 (m, 30H), 4.76 (m, 1H), 4.44 (m, 1H), 4.35 (m, 1H).

Fuente