HCID 18647802, Verbindung → 3'-Azido-3'-deoxy-4-thiothymidine

Reaktionsgleichung

[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10]C(=O)C)[O:7][C@@H:6]([N:14]2[CH:22]=[C:20]([CH3:21])[C:18](=[S:19])[NH:17][C:15]2=[O:16])[CH2:5]1)=[N+:2]=[N-:3]>O1CCOCC1.[NH4+].[OH-].CCOCC>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:14]2[CH:22]=[C:20]([CH3:21])[C:18](=[S:19])[NH:17][C:15]2=[O:16])[CH2:5]1)=[N+:2]=[N-:3]

Komponenten

Versuchsvorschrift

3'-Azido-3'-deoxy-5'-O-acetyl-4-thiothymidine (0.25 g; 0.76 mMol, Example 21) was dissolved in a mixture of 5 mL of dioxane and 5 mL of conc. NH4OH and stirred for 18 hrs. The solvent was removed in vacuo and the residue applied to a silica gel column followed by elution with CHCl3 /EtOAc (3:1 v/v). The appropriate fractions were combined and the solvent removed in vacuo to yield a yellow oil which was dissolved in Et2O, forming crystals upon concentration: 0.16 g (0.56 mMol; 74%); m.p.=116°-118° C.