25775-85-3Relevant articles and documents
Regioselective 1-N-Alkylation and rearrangement of adenosine derivatives
Oslovsky, Vladimir E.,Drenichev, Mikhail S.,Mikhailov, Sergey N.
, p. 475 - 499 (2015/10/19)
Several methods for the preparation of some N6-substituted adenosines based on selective 1-N-alkylation with subsequent Dimroth rearrangement were developed. The proposed methods seem to be effective for the preparation of natural N6-isopentenyl- and N6-benzyladenosines, which are known to possess pronounced biological activities. Direct 1-N-alkylation of 2′,3′,5′-tri-O-acetyladenosine and 3,5′-di-O-acetyl-2-deoxyadenosine with alkyl halides in N,N-dimethylformamide (DMF) in the presence of BaCO3 and KI gave 1-N-substituted derivatives with quantitative yields, whereas 1-N-alkylation of adenosine was accompanied by significant O-alkylation. Moreover, the reaction of trimethylsilyl derivatives of N6-acetyl-2,3,5′-tri-O-acetyladenosine and N6-acetyl-3,5′-di-O-acetyl-2-deoxyadenosine with alkyl halides leads to the formation of the stable 1-N-substituted adenosines. Dimroth rearrangement of 1-N-substituted adenosines in aqueous ammonia yields pure N6-substituted adenosines.
