p-Toluenesulfonic acid → 2',3'-Didehydro-2',3'-dideoxyuridine

HRID 249056

반응식

HRID 249056 반응식
C([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:34]=[CH:33][C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH:24]=[CH:23]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C(Cl)(Cl)Cl.CO>[C@@H:25]1([N:27]2[CH:34]=[CH:33][C:31](=[O:32])[NH:30][C:28]2=[O:29])[O:26][C@H:22]([CH2:21][OH:20])[CH:23]=[CH:24]1

참가 물질

6

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 110916535'O-trityl-2',3'-dideoxy-2',3'-didehydrouridine

생성물 1

HCID 651592',3'-Didehydro-2',3'-dideoxyuridine

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

5'O-trityl-2',3'-dideoxy-2',3'-didehydrouridine (0.5 gm.,1.1 mM) was dissolved in a chloroform (10 mL) and methanol (2 mL) mixture containing 2% p-toluenesulphonic acid. The reaction mixture was stirred at room temperature for 0.75 hr., and then neutralized with 2N NaOH (0.5 mL). The solvent was removed in vacuo and the residue chromatographed on silica using chloroform/acetone (2:1) as eluent. The desired product was isolated as a white crystalline solid with the same physical and spectroscopic characteristics as d4U produced by an alternative method. M.p. 155° C. 1H NMR (360 Mhz, D2O/DMSO) 7.8 (d, 1H, H6), 6.7 (m, 1H, H1'), 6.37 (m, 1H, H2'), 5.8 (m, 1H, H3'), 5.56 (d, 1H, H5), 4.7 (m, 1H, H4'), 3.6 (m, 2H, H5'). 13C NMR (70 Mhz, D2O/DMSO) 163 (C4), 151 (C2), 141 (C2'), 135 (C3'), 126 (C6), 101 (C5), 89 (C1'), 87 (C4'), 62 (C5').

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue chromatographed on silica

출처 및 근거

ORD 기록
ord-7594f2a196c44593b7c5773cc7805d8c
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05212294

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