2,6-Lutidine → (2S,3S)-4-(allyloxy)-3-(tert-butoxycarbonyl)-2-(tert-butyldimethylsilyloxy)butyl acetate

Participants

Reaction Conditions

Reaction Steps

The crude material from Step 2 (0.090 g) was dissolved in CH2Cl2 (3 mL) and cooled to 0° C. To the cooled solution, was added 2,6-lutidine (0.10 mL, 0.90 mmol) followed by TBSOTf (0.10 mL, 0.4 mmol). The mixture was stirred at 0° C. for 2 h then diluted with H2O and sat'd NaHCO3. The aqueous phase was extracted with CH2Cl2 (3×20 mL) and the organic extracts dried (Na2SO4), filtered, and conc in vacuo. Purification on SiO2 (5-20% EtOAc/Hexanes) gave the title compound as a yellow oil.

Provenance & Evidence