A convenient procedure for the synthesis of theophylline nucleosides

Reactions of Transglycosylation in the Nucleoside Chemistry

“…However, any modification of the 6-oxopurine system may drastically change the product distribution, as it has been presented above for O 6 -substitution (only 9-isomers). In turn, 3-alkylation shifts the transglycosylation equilibrium towards the 7-regiosomers, as it has been demonstrated for 3-benzylinosine [82], theophylline nucleosides [57,83,84], 3-methylguanosine [85], and structurally related wyosine [7,86,87]. The exclusive formation of 7-regioisomers can be rationalized here by a greater thermodynamic stability of 3,7-disubstituted purines versus 3,9-disubstitution, at least for steric reasons.…”

Synthesis of 3 - 3 - gem - di - C -Nitromethyl Nucleoside Analogues of Possible Biological Activity

“…were prepared as previously (7) . 3 -Deoxy -1,2 :5,6di -Oisopropylidone -3 -Cnitromethylene --Dribohexofuranose (4) was prepared according to the method described (21) .Bis (theophylline -7 yl )mercury (10) was prepared as in the method described (12) .2,4 -Bis (trimethylisly uracial (13) was synthesized as described before (15) . 5) (8.3g, 22.9 mmol ) was dissolved in methanol and IN H 2 SO 4 (30ml) was added .…”

“…For the synthesis of 7 (12 ) , the Koenigs -Knorr condensation method was followed (10) . Thus treatment of 1,2 -di -Oacetylrlbofuranose derivative (9) with anhydrous hydrogen bromide in dichloromethane readily afforded 1,2di -O bromide (11) which was used immediately because of its instability .…”

Synthesis of New Nucleoside Analogues from Theobromine

“…[1] [31] This compound were prepared according literature (31) with some modification. Theobromine (1 g, 5.49 mmol) was dissolved in hot water (30 mL) and sodium hydroxide (0.4 g, 5.2 mmol) was added, to vigorously stirred solution of mercuric chloride (0.82 g, 2.6 mmol) in hot ethanol (50 mL).…”