Abstract
An efficient protection protocol for the 6-exo-amino group of purine nucleosides with various chloroformates was developed utilizing N-methylimidazole (NMI). The reaction of an exo-N(6)-group of adenosine analogue 1 with alkyl/and aryl chloroformates under optimized conditions provided the N(6)-carbamoyl adenosines (2a-j) in good to excellent yields. The reaction of N(6)-Cbz-protected nucleosides (5a-c) with phenyl phosphoryl chloride (7) using t-BuMgCl followed by catalytic hydrogenation afforded the corresponding phosphoramidate pronucleotides (8a-c) in excellent yield.
Publication types
-
Research Support, N.I.H., Extramural
-
Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
-
Adenosine Monophosphate / analogs & derivatives*
-
Adenosine Monophosphate / chemical synthesis*
-
Adenosine Monophosphate / chemistry
-
Amides / chemical synthesis*
-
Amides / chemistry
-
Combinatorial Chemistry Techniques
-
Imidazoles / chemistry
-
Molecular Structure
-
Nucleosides / chemical synthesis*
-
Nucleosides / chemistry
-
Phosphoric Acids / chemical synthesis*
-
Phosphoric Acids / chemistry
-
Prodrugs / chemical synthesis*
-
Prodrugs / chemistry
-
Purine Nucleosides / chemistry
Substances
-
Amides
-
Imidazoles
-
Nucleosides
-
Phosphoric Acids
-
Prodrugs
-
Purine Nucleosides
-
Adenosine Monophosphate
-
phosphoramidic acid
-
1-methylimidazole