REACTION OF URIDINES AND THYMIDINES WITH METHYL PROPYNOATE - A NEW N-3 PROTECTING GROUP

Authors
FAJA M ARIZA X GALVEZ C VILARRASA J
Citation
M. Faja et al., REACTION OF URIDINES AND THYMIDINES WITH METHYL PROPYNOATE - A NEW N-3 PROTECTING GROUP, Tetrahedron letters, 36(18), 1995, pp. 3261-3264
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
18
Year of publication
1995
Pages
3261 - 3264
Database
ISI
SICI code
0040-4039(1995)36:18<3261:ROUATW>2.0.ZU;2-U
Abstract
A fast conjugated addition takes place when uridines and thymidines ar e treated with HC-C-COOMe in the presence of suitable bases such as DM AP. As the resulting N-CH=CH-COOMe moiety appears to be very stable un der acidic conditions, but it is readily cleaved by nucleophiles such as pyrrolidine or methylamine, a new protection protocol for N-3 of ur idines and thymidines is disclosed.