Reacción #74464

Ecuación de reacción

2,3,4,6-tetra-O-benzyl-D-glucopyranone

gluconolactone

compound 2

gluconolactone

(5-Bromo-2-chlorobenzyloxy)triisopropylsilane

compound 4

(5-Bromo-2-chlorobenzyloxy)triisopropylsilane

n-butyllithium

→

title compound

(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-3-((triisopropylsilyloxy)methyl)phenyl)-tetrahydro-2H-pyran-2-ol

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for 3 h at the same temperature
2. 2
   OtroThe reaction mixture was quenched by addition of saturated ammonium chloride solution
3. 3
   workup.ADDITIONAfter complete addition
4. 4
   OtroThe organic layer was separated
5. 5
   Extracciónthe aqueous layer was extracted with ethyl acetate
6. 6
   LavadoThe combined organic layers were washed with brine
7. 7
   Secadodried over magnesium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated in vacuo

Procedimiento

To a solution of (5-Bromo-2-chlorobenzyloxy)triisopropylsilane (compound 4, 97 g, 257 mmol) from Step 3 in tetrahydrofuran (1 L) at −78° C. under an atmosphere of nitrogen was added dropwise n-butyllithium (2.5 M in hexanes, 103 mL, 257 mmol), and the mixture was stirred for 1.5 h at the same temperature. Then a solution of 2,3,4,6-tetra-O-benzyl-D-glucopyranone (compound 2, 106 g, 198 mmol) from Step 1 in tetrahydrofuran (500 mL) was added dropwise, and the mixture was stirred for 3 h at the same temperature. The reaction mixture was quenched by addition of saturated ammonium chloride solution. After complete addition, the solution was gradually raised to room temperature. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound as a yellow oil which was used without further purification.

Fuente