8-Bromo-2'-deoxyadenosine → 2'-Deoxy-8-methoxyadenosine

HRID 2050604

반응식

HRID 2050604 반응식
Br[C:2]1[N:3]([C:12]2[N:13]=[CH:14][N:15]=[C:16]([NH2:19])[C:17]=2[N:18]=1)[C@@H:4]1[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[CH2:5]1.[CH3:20][O-:21].[Na+]>CO>[CH3:20][O:21][C:2]1[N:3]([C:12]2[N:13]=[CH:14][N:15]=[C:16]([NH2:19])[C:17]=2[N:18]=1)[C@@H:4]1[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[CH2:5]1

참가 물질

4

반응물 2

HCID 965478-Bromo-2'-deoxyadenosineHCID 10942334Sodium Methoxide

생성물 1

HCID 539094342'-Deoxy-8-methoxyadenosine수율 55%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 8-bromo-2'-deoxyadenosine (1.85 g, 5.61 mmol) in methanol (100 ml) was added sodium methoxide (0.908 g, 16.8 mmol), and the mixture was refluxed for 20 h. The solvent was evaporated and the residue chromatographed on silica gel (5% methanol/chloroform) to give 0.865 g (55%) of 2'-deoxy-8-methoxyadenosine: 1H NMR (Me2SO-d6) δ2.11 (m, 2H), 3.53 (m, 2H), 3.81 (m, 1H), 4.10 (s, 3H), 4.38 (m, 1H), 5.24 (m, 2H), 6.18 (t, 1H, J=6.8 Hz), 6.89 (br.s, 2H), 8.02 (s, 1H); UV (H2O) λmax 261 nm. 2'Deoxy-8-methoxyadenosine was converted to 2',3'-dideoxy-8-methoxydenosine (IX) by using in sequence Procedures A (64%), D (83%), and E and F (79%): mp 197°-799° C.; 13C NMR (Me2SO-d6) δ27.0, 28.9, 57.2, 64.0, 81.1, 83.3, 114.8, 148.8, 150.7, 153.9, 154.3; 1H NMR (Me2SO-d6) δ2.16 (m, 4H), 3.51 (m, 2H), 4.10 (br.s, 4H), 5.01 (m, 1H), 6.08 (m, 1H), 6.85 (br.s, 2H), 8.03 (s, 1H); UV (H2O) λmax 260 nm (ε11040); FAB HRMS obsd (M+ +H) 266.1273, calcd for C11H15N5O3 266.1253.

후처리

  1. temperaturethe mixture was refluxed for 20 h
  2. customThe solvent was evaporated
  3. customthe residue chromatographed on silica gel (5% methanol/chloroform)

출처 및 근거

ORD 기록
ord-ecc0d45573024d54b4bc0f7b8f92c3d3
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05013829

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