تفاعل #48322

معادلة التفاعل

NaHCO3

2,6-lutidine

crude material

(2S,3S)-4-(allyloxy)-3-(tert-butoxycarbonyl)-2-hydroxybutyl acetate

TBSOTf

→

title compound

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

المذيبات

H2O

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe aqueous phase was extracted with CH2Cl2 (3×20 mL)
2. 2
   تجفيفthe organic extracts dried (Na2SO4)
3. 3
   ترشيحfiltered
4. 4
   أخرىPurification on SiO2 (5-20% EtOAc/Hexanes)

الإجراء التجريبي

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.

المصدر