تفاعل #47754

معادلة التفاعل

diethyl azodicarboxylate

Compound 16

5-Acetylamino-3-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidine-2,7-dione

triphenylphosphine resin

Isopropanol

→

27

المردود 65.2%

5-Acetylamino-7-isopropoxy-3-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one

المردود 65.2%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe flask was removed from the ice bath
2. 2
   درجة الحرارةto warm to ambient temperature
3. 3
   أخرىUpon consumption of 16
4. 4
   ترشيحwas filtered off
5. 5
   أخرىThe crude reaction mixture
6. 6
   أخرىwas purified by flash chromatography
7. 7
   أخرىRemoval of the solvent

الإجراء التجريبي

Compound 16 (650 mg, 1.34 mmol) and Argonaut PS-triphenylphosphine resin (4.02 mmol, 1.86 g) were placed under a dry nitrogen atmosphere in a flame-dried flask, and then dry THF (20 ml) was added. The flask was then cooled to 0° C. in an ice bath. Isopropanol (IPA) (0.20 ml, 2.68 mmol) was added followed by the dropwise addition of diethyl azodicarboxylate (DEAD) (0.366 ml, 2.0 mmol). The flask was removed from the ice bath and allowed to warm to ambient temperature. The reaction mixture was monitored for the disappearance of compound 16 by TLC. Upon consumption of 16, the solid supported material was filtered off. The crude reaction mixture was purified by flash chromatography using a 15 to 60% gradient of ethyl acetate in chloroform. Removal of the solvent afforded 460 mg (64.9%) of 27 as a white foam: MS (+)-ES [M+H]+ m/z 527. Rf=0.7 (75% Ethyl acetate -CHCl3).

المصدر