Reacción #6156

Ecuación de reacción

(3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one

t-butyldimethylchlorosilane

ether

→

(3S,4S,6R)-tetrahydro-3-hexyl-4-[(t-butyldimethylsilyl)oxy]-6-undecyl-2H-pyran-2-one

Rendimiento 63.5%

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixtures
2. 2
   Lavadowashed with 1N hydrochloric acid
3. 3
   OtroThe organic phase was dried
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated
6. 6
   OtroThe material obtained
7. 7
   Otrowas chromatographed on silica gel

Procedimiento

M)d) 1.5 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one were dissolved in 8 ml of DMF. 0.85 g of t-butyldimethylchlorosilane in 4 ml of DMF were then added dropwise. The mixture was stirred for 48 hours. The reaction mixtures was poured in to 100 ml of ether and washed with 1N hydrochloric acid. The organic phase was dried, filtered and evaporated. The material obtained was chromatographed on silica gel. There was obtained 1.26 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-[(t-butyldimethylsilyl)oxy]-6-undecyl-2H-pyran-2-one, MS: 411 (M+ -t-butyl).

Fuente