Novel nucleoside analogs were synthesized, in which (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol bears the nucleobase exploiting a 1-oxoethane-1,2-diyl group. Within this synthetic approach, cleavage of the N-phenylethyl group in the starting compound and introduction of the nucleobase-bearing amidic chain were accomplished with a one-pot procedure, simply using bromoacetyl bromide. Moreover, the benzyl carbonate protecting group was used to obtain easy to handle compounds and avoid deprotection of nucleobases occurring under basic conditions. Eventually, directed towards the preparation of short oligonucleotide sequences, both hydroxy functionalities of the iminosugar were orthogonally protected as benzyl carbonate and dimethoxytrityl ether, respectively. Then, exploiting selective orthogonal deprotections and subsequent use of the phosphoramidite method, a dimer phosphite was synthesized, verifying the possibility of building oligomeric structures displaying these novel nucleoside analogs.
Novel nucleoside analogs tethered on (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol / Amici, Adolfo; Martelli, Gianluca; Orena, Mario; Rinaldi, Samuele. - In: JOURNAL OF THE IRANIAN CHEMICAL SOCIETY (PRINT). - ISSN 1735-207X. - STAMPA. - 12:4(2015), pp. 655-665. [10.1007/s13738-014-0524-5]