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

HRID 2050604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2050604
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 539094342'-Deoxy-8-methoxyadenosineAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ecc0d45573024d54b4bc0f7b8f92c3d3
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05013829

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