تفاعل #1994272

معادلة التفاعل

( 2 )

5′-O-(tert-butyidimethylsilyl)-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2′-deoxyuridine

acetic acid

acetic anhydride

DMSO

→

oil

المردود 89.0%

5′-O-(tert-Butydimethylsilyl)-3′-O-methylthiomethyl-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2′-deoxyuridine

المردود 89.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىwas quenched with sat. aq. NaHCO3
2. 2
   workup.ADDITIONEtOAc (50 ml) was added
3. 3
   استخلاصthe aqueous layer was extracted three times with ethyl acetate
4. 4
   غسيلThe combined organic layers were washed with sat. aq. NaHCO3 solution
5. 5
   تجفيفdried (MgSO4)
6. 6
   أخرىAfter removing the solvent under reduced pressure
7. 7
   أخرىthe product (3) was purified by chromatography on silica (EtOAc: petroleum ether 8:2)

الإجراء التجريبي

To a solution of (2) (1.84 g, 3.7 mmol) in dry DMSO (7 ml) was added acetic acid (3.2 ml) and acetic anhydride (10.2 ml). The mixture was stirred for 2 days at room temperature, before it was quenched with sat. aq. NaHCO3. EtOAc (50 ml) was added and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with sat. aq. NaHCO3 solution and dried (MgSO4). After removing the solvent under reduced pressure, the product (3) was purified by chromatography on silica (EtOAc: petroleum ether 8:2) yielding a clear sticky oil (1.83 g, 89%). 1H NMR (d6 DMSO): δ 0.00 (s, 6H, CH3), 0.79 (s, 9H, tBu), 1.96-2.06 (m, 1H, H-2′), 1.99 (s, 3H, SCH3), 2.20-2.26 (m, 1H, H-2′), 3.63-3.74 (m, 2H, H-5′), 3.92-3.95 (m, 1H, H-4′), 4.11-4.13 (m, 2H, CH2), 4.28-4.30 (m, 1H, H-3′), 4.59 (br s, 2H, CH2), 5.97 (t, J=6.9 Hz, 1H, H-1′), 7.85 (s, 1H, H-6), 9.95 (t, J=5.3 Hz, 1H, NH), 11.64 (s, 1H, NH). Mass (−ve electrospray) calcd for C22H32F3N3O6SSi 551.17. Found 550.

المصدر