Download PDF
Synlett 1993; 1993(3): 221-222
DOI: 10.1055/s-1993-22410
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Novel p-Toluenesulfonylation and Thionocarbonylation of Unprotected Thymine Nucleosides

Annie Grouiller* , Véronique Buet, Valérie Uteza, Gérard Descotes
  • *Université Lyon I, Laboratoire de Chimie organique II, Bât. 308, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France
Further Information

Publication History

Publication Date:
19 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

A new procedure involving the use of both dibutyltin oxide and a quaternary ammonium salt along with p-toluenesulfonyl chloride or phenoxythiocarbonyl chloride leads in good yields to the desired monotosylate or to the 2′,3′-O -cyclic thiocarbonate of thymine nucleosides without prior modification of any hydroxyl group. It is noteworthy that with 5-methyl uridine, tosylation occurs regioselectively at the 2′- position, while the 3′-O-tosylate is formed when 5-methyl uridine is substituted on 1′ by a methyl (or cyano) group.