4-Toluenesulfonyl chloride → 5'-Azidoguanosine

HRID 847441Notes

Reaction equation

HRID 847441 reaction equation
NC[C@H]1O[C@@H](N2C3N=C(N)NC(=O)C=3N=C2)C[C@@H]1O.[C@@H:20]1([N:28]2[C:38]3[N:37]=[C:35]([NH2:36])[NH:34][C:32](=[O:33])[C:31]=3[N:30]=[CH:29]2)[O:27][C@H:24]([CH2:25][OH:26])[C@@H:22]([OH:23])[CH2:21]1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.S(C1C=CC(C)=CC=1)([O-])(=O)=[O:51].[N-:61]=[N+:62]=[N-:63].[Na+]>N1C=CC=CC=1.CN(C=O)C>[N:61]([CH:25]([OH:26])[C@H:24]1[O:27][C@@H:20]([N:28]2[C:38]3[N:37]=[C:35]([NH2:36])[NH:34][C:32](=[O:33])[C:31]=3[N:30]=[CH:29]2)[C@H:21]([OH:51])[C@@H:22]1[OH:23])=[N+:62]=[N-:63]

Participants

8

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 33557Sodium AzideHCID 85570p-ToluenesulfonateHCID 135398592DeoxyguanosineHCID 1358167395'-Amino-2',5'-dideoxyguanosine

Product 1

HCID 1364033885'-Azidoguanosine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

An alternate preparation of 5'-amino-2',5'-dideoxyguanosine is to treat the protected 2'-deoxyguanosine (protected at either the N-2-phenylacetyl or the N-2-FMOC derivative) (1 mmol) with tosyl chloride (1.3 mmol) in pyridine at 0° C. overnight. The solution is evaporated to dryness and the residue is dissolved in chloroform. The resulting solution is washed twice with aqueous sodium bicarbonate and dried over sodium sulfate. The solvent is evaporated and the residue chromatographed on silica gel eluting with methanol/chloroform mixtures. The resulting tosylate (1 mmol) is treated with sodium azide (6 mmol) in DMF at 80°-100° C. for a few h. The solvent is removed by rotovap and the residue is chromatographed on silica gel eluting with chloroform/ methanol solvent mixtures. The azide is reduced to the desired amine using the catalytic hydrogenation procedure above.

Workup

  1. customat 0° C.
  2. customovernight
  3. customThe solution is evaporated to dryness
  4. dissolutionthe residue is dissolved in chloroform
  5. washThe resulting solution is washed twice with aqueous sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is evaporated
  8. customthe residue chromatographed on silica gel eluting with methanol/chloroform mixtures
  9. customThe solvent is removed by rotovap
  10. customthe residue is chromatographed on silica gel eluting with chloroform/ methanol solvent mixtures

Sources & evidence

ORD record
ord-a4b982b8ea954efdb3653c8c755cbf28
Source dataset
uspto-grants-1992_08
Patent number
US05142047

Reaction notes

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