Stereocontrolled synthesis of dinucleoside phosphorothioates using a fluorous tag

• Published in: Journal of fluorine chemistry Vol. 150; pp. 85 - 91
• Main Authors: Oka, Natsuhisa, Murakami, Ryosuke, Kondo, Tomoaki, Wada, Takeshi
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.06.2013; Elsevier
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Fluorous; Oxazaphospholidine; Phosphorothioate; Physical Sciences; Science & Technology; Stereocontrolled synthesis; Fluorous; Phosphorothioate; Stereocontrolled synthesis; Oxazaphospholidine; SILICA-GEL; SOLID-PHASE SYNTHESIS; BORANOPHOSPHATES; DNA; OLIGOSACCHARIDE SYNTHESIS; OXAZAPHOSPHOLIDINE APPROACH; C-ELEGANS; SILYL PROTECTING GROUP; STEREOSELECTIVE-SYNTHESIS; OLIGONUCLEOSIDE PHOSPHOROTHIOATES
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2013.03.013

Dinucleoside phosphorothioates were synthesized in a stereocontrolled manner with diastereoselectivity of >99:1 by using simple perfluoroalkyl groups as fluorous tags. •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.