تفاعل #71578

معادلة التفاعل

Compound 6

6-O-(4,4′-dimethoxytrityl)-2-deoxy-2(thymin-1yl]-3-O-(2-fluoroethyl)D-altro-hexitol

imidazole

P2O5

chloro triethylsilane

→

Compound 8

المردود 82.5%

6-O-(4,4′-dimethoxytrityl)-3-O-(2-fluoroethyl)-4-O-(triethylsilyl)-2-deoxy-2-(thymin-1yl)-D-altro-hexitol

المردود 82.5%

المذيبات

DMF

EtOAc

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with sat. NaHCO3 (100 mL) and brine (50 mL)
2. 2
   تجفيفthen dried over anhydrous Na2SO4
3. 3
   ترشيحfiltered
4. 4
   أخرىevaporated
5. 5
   أخرىThe residue was purified by silica gel column chromatography (50% EtOAc in hexanes)

الإجراء التجريبي

Compound 6, prepared as per the procedures illustrated in Example 13 (2.50 g, 4.00 mmol) was mixed with imidazole (1.36 g, 20.0 mmol) over P2O5 under reduced pressure. This mixture was dissolved in anhydrous DMF (13 mL) and chloro triethylsilane (1.71 mL, 10 mmol) was added. The mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted in EtOAc (100 mL), washed with sat. NaHCO3 (100 mL) and brine (50 mL) then dried over anhydrous Na2SO4, filtered and evaporated. The residue was purified by silica gel column chromatography (50% EtOAc in hexanes) to yield Compound 8 (2.45 g, 82.5%) as a white foam. MS (ES): m/z 760.2 [M+Na]+.

المصدر