N-ACYL PROTECTING GROUPS FOR DEOXYNUCLEOTSIDES A QUANTITATIVE AND COMPARATIVE STUDY

Article abstract of DOI:10.1016/S0040-4020(01)92022-8

A detailed study in search for suitable N-acyldeoxy-nucleosides which could serve as building blocks for the stepwise synthesis of deoxyoligonucleotides was undertaken.Several acyl groups namely 4-t-butylphenylacetyl, 4-t-butylphenoxyacetyl, 4-chlorobenzoyl, 3,4-dichlorobenzoyl, 2-methyl-benzoyl, 2,4-dimethylbenzoyl, nicotinoyl, 4-t-butylbenzoyl and 4-phenylazobenzoyl have been used for the protection of the exocyclic amino groups of deoxynucleosides.Interesting data concerning the stability of N-acyl groups towards a potent deacylating system (0.2N NaOH/MeOH) are presented.