반응 #1994272

반응 방정식

( 2 )

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

acetic acid

acetic anhydride

DMSO

→

oil

수율 89.0%

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

수율 89.0%

반응 조건

후처리

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

실험 절차

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.

출처