Reaction #48323

Reaction equation

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

Solvents

CH2Cl2

EtOAc

NaHCO3

Na2S2O3

Conditions

Workup

1. 1
   workup.STIRRINGThe biphasic mixture was stirred until it
2. 2
   WashThe organic layer was washed with brine
3. 3
   Dryingdried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   OtherThe crude aldehyde was used without further purification

Procedure

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.

Source