A CONVENIENT METHOD FOR THE SYNTHESIS AND RANEY-NICKEL DESULFURIZATION OF 5'-DEOXY-5'-METHYLTHIOADENOSINE

Authors
SCOVILL JP THIGPEN DL LEMLEY PV
Citation
Jp. Scovill et al., A CONVENIENT METHOD FOR THE SYNTHESIS AND RANEY-NICKEL DESULFURIZATION OF 5'-DEOXY-5'-METHYLTHIOADENOSINE, Phosphorus, sulfur and silicon and the related elements, 85(1-4), 1993, pp. 149-152
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Phosphorus, sulfur and silicon and the related elements → ACNP
ISSN journal
10426507
Volume
85
Issue
1-4
Year of publication
1993
Pages
149 - 152
Database
ISI
SICI code
1042-6507(1993)85:1-4<149:ACMFTS>2.0.ZU;2-8
Abstract
A convenient procedure for the preparation of 5'-deoxy-5'-methylthioad enosine is reported. Chlorination of adenosine with thionyl chloride y ielded 5'-chloro-5'-deoxyadenosine. Reaction of 5'-chloro-5'-deoxyaden osine with aqueous methylmercaptide anion yielded 5'-deoxy-5'-methylth ioadenosine. Hydrogenolysis of 5'-deoxy-5'-methylthioadenosine over Ra ney nickel in water produced 5'-deoxyadenosine. This procedure affords a high yield of readily purified 5'-deoxyadenosine while avoiding the use of anhydrous solvents and pyrophoric reagents. The procedure illu strates the utility of sulfur reagents to accomplish high value added transformations in nucleoside chemistry.