Reacción #48323

Ecuación de reacción

crude material

Tert-butyl (2S,3S)-1-(allyloxy)-3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-ylcarbamate

Dess-Martin periodinane

→

Tert-butyl (2S,3S)-1-(allyloxy)-3-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate

Disolventes

CH2Cl2

EtOAc

NaHCO3

Na2S2O3

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe biphasic mixture was stirred until it
2. 2
   LavadoThe organic layer was washed with brine
3. 3
   Secadodried (Na2SO4)
4. 4
   Filtraciónfiltered
5. 5
   OtroThe crude aldehyde was used without further purification

Procedimiento

The crude material from Step 4 (0.040 g) was dissolved in CH2Cl2 (3 mL) and treated with Dess-Martin periodinane (0.07 g, 0.2 mmol). The mixture was stirred at ambient temperature for 4 h then diluted with EtOAc (10 mL), sat'd NaHCO3 (5 mL), and aqueous Na2S2O3 (5 mL). The biphasic mixture was stirred until it was colorless. The organic layer was washed with brine, dried (Na2SO4), filtered, and conc in vacuo. The crude aldehyde was used without further purification.

Fuente