Stereocontrolled synthesis of dinucleoside phosphorothioates using a fluorous tag

•Dinucleoside phosphorothioates were synthesized in a stereocontrolled manner (diastereoselectivity >99:1).•Thymidine derivatives bearing a simple perfluoroalkyl tag (C6F13 or C8F17) at the 3′-end and diastereopure nucleoside 3′-O-oxazaphospholidine monomers were used.•Fluorous-tagged intermediates in the synthesis were easily purified by a simple fluorous solid-phase extraction process.

Dinucleoside phosphorothioates were synthesized in a stereocontrolled manner (diastereoselectivity > 99:1) by using thymidine derivatives bearing a simple perfluoroalkyl tag (C6F13 or C8F17) at the 3′-end and diastereopure nucleoside 3′-O-oxazaphospholidine monomers. Fluorous-tagged intermediates in the synthesis were easily purified by a simple fluorous solid-phase extraction process.

Graphical abstractDinucleoside phosphorothioates were synthesized in a stereocontrolled manner with diastereoselectivity of >99:1 by using simple perfluoroalkyl groups as fluorous tags.Figure optionsDownload full-size imageDownload as PowerPoint slide