反応 #2175446

反応方程式

23-Azido-3,6,9,12,15,18,21-heptaoxatricosan-1-ol

DAST

→

4

収率 24.4%

23-azido-1-fluoro-3,6,9,12,15,18,21-heptaoxatricosane

収率 24.4%

溶媒

DCM

反応条件

後処理

1. 1
   温度to warm to room temperature
2. 2
   workup.STIRRINGstirred for additional 20 hours
3. 3
   その他The excess of DAST was quenched with methanol (5 mL)
4. 4
   その他the solvents were subsequently evaporated at the reduced pressure
5. 5
   workup.DISSOLUTIONThe oily residue was dissolved in the water (3 mL)
6. 6
   その他The crude product was purified on semipreparative HPLC (System E)

実験手順

23-Azido-3,6,9,12,15,18,21-heptaoxatricosan-1-ol (500 mg, 1.26 mmol) was dissolved in DCM (2 mL) and cooled to −10° C. DAST (482 μL, 3.78 mmol) was added in portions to the cooled solution and the resulting mixture was stirred at −10° C. for 30 minutes then allowed to warm to room temperature and stirred for additional 20 hours. The excess of DAST was quenched with methanol (5 mL) and the solvents were subsequently evaporated at the reduced pressure. The oily residue was dissolved in the water (3 mL) and the pH was adjusted to 5 using NaHCO3. The crude product was purified on semipreparative HPLC (System E) to yield 122 mg (24%) of 4 as a yellowish oil. 1H NMR (500 MHz, CDCl3): δ 3.39 (t, J=5.0 Hz, 2H), 3.65-3.68 (m, 26H), 3.75 (dt, J=4.2 Hz, 29.6 Hz, 2H), 4.56 (dt, J=4.0 Hz, 47.5 Hz, 2H); 13C NMR (125.7 MHz, CDCl3): δ 50.8, 70.1, 70.4, 70.5, 70.7-70.8, 70.9, 83.2 (d, J=169 Hz); 19F NMR (470.6 MHz, CDCl3): 6-225.9; MS ESI (m/z): [M+H]+ calcd. for C16H33FO7N3, 398.2; found 398.0.

出典