Synthesis of 2′, 3′ -Dideoxy-6, 3′-Methano-cyclouridine and a Furanosyl To Pyranosyl Ring-isomerization In The C-cyclo-nucleoside (Nucleosides and Nucleotides. 53¹)

3 January 1984

journal article
research article
Published by Taylor & Francis in Nucleosides, Nucleotides and Nucleic Acids

Vol. 3 (3) , 295-302
https://doi.org/10.1080/07328318408081266

Abstract

Synthesis of a C-cyclouridine fixed by a 6,3''-methylene unit, 2'',3''-dideoxy-6,3''-methano-cyclouridine, was accomplished by utilizing a 3''-hydroxymethyluridine via an intramolecular radical addition as the key step. A furanosyl to pyranosyl ring-isomerization was observed in this reparation and the mechanism for this isomerization is presented. [These compounds have possible antiviral and antitumor activities.].

This publication has 2 references indexed in Scilit:

Synthesis of 5-Alkyl- and 5-Acyl-uridines via 6-Mercaptouridine (Nucleosides and Nucleotides. XVII)
HETEROCYCLES, 1977
The base catalysed anomerisation of -5-formyluridine; crystal and molecular structure of -5-formyluridine
Nucleic Acids Research, 1976

Synthesis of 2′, 3′ -Dideoxy-6, 3′-Methano-cyclouridine and a Furanosyl To Pyranosyl Ring-isomerization In The C-cyclo-nucleoside (Nucleosides and Nucleotides. 531)

Abstract

Synthesis of 2′, 3′ -Dideoxy-6, 3′-Methano-cyclouridine and a Furanosyl To Pyranosyl Ring-isomerization In The C-cyclo-nucleoside (Nucleosides and Nucleotides. 53¹)