تفاعل #1994280

معادلة التفاعل

material ( 15 )

4-N-Benzoyl-5′—O-(tert-butyldimethylsilyl)-3′-O-azidomethyl-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2′-deoxycytidine

TBAF

→

desired product ( 16 )

4-N-Benzoyl-3′-O-azidomethyl-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2′-deoxycytidine

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىVolatile material removed under reduced pressure
2. 2
   أخرىto yield a brown gel that
3. 3
   أخرىwas purified by flash chromatography (EtOAc:DCM 7:3)

الإجراء التجريبي

The starting material (15) (140 mg, 0.22 mmol) was dissolved in THF (7.5 ml). TBAF (1M soln. in THF, 0.25 ml) was added slowly and stirred for 2 h at room temperature. Volatile material removed under reduced pressure to yield a brown gel that was purified by flash chromatography (EtOAc:DCM 7:3) to yield the desired product (16) as a light coloured crystalline solid (0.9 g, 76%). 1H NMR (d6 DMSO): δ 2.16 (m, 1H, H-2′), 2.22 (m, 1H, H-2′), 3.70 (d, 1H, J=11.5 Hz, H-5′), 3.75 (d, 1H, J=11.3 Hz, H-5′), 4.01 (m, 1H, H-4′), 4.10 (m, 1H, CH2NH), 4.23 (m, 1H, H-3′), 4.76 (s, 2H, CH2S), 5.32 (s, 1H, 5′OH), 5.99 (m, 1H, H-1′), 7.37 (m, 2H, Ph), 7.50 (m, 2H, Ph), 7.81 (d, 1H, J=7.35 Hz, Ph), 7.95 (s, 1H, H-6), 9.78 (br s, 1H, NHCH2), 12.64 (br s, 1H, NH). Mass (−ve electrospray) calcd for C22H20F3N7O6 535.44. Found 534.

المصدر