A versatile approach to the synthesis of dinucleotide analogs containing neutral 5'-thioformacetal internucleoside linkages

Article abstract of DOI:10.1016/00404-0399(50)1393-V

Activation of nucleoside donors 5 by sulfuryl chloride followed by the addition of 5'-thionucleoside acceptors 3 yields 5'-thioformacetal dinucleotide analogs 6 with in situ trapping of liberated methanesulfenyl chloride with cyclohexene. Purine as well as pyrimidine derivatives can be part of a coupling reaction as nucleoside donors or acceptors. The dimethoxytrityl protecting group is compatible with the present coupling methodology allowing differential 3',5'-end protection with concomitant orthogonal base protection.