SYNTHESIS AND CONFIGURATIONAL ASSIGNMENTS OF 3-SUBSTITUTED 2-DEOXY-4-THIO-D-ERYTHRO-PENTOFURANOSE DERIVATIVES

Authors
AITSIR H FAHMI NE GOETHALS G RONCO G TBER B VILLA P EWING DF MACKENZIE G
Citation
H. Aitsir et al., SYNTHESIS AND CONFIGURATIONAL ASSIGNMENTS OF 3-SUBSTITUTED 2-DEOXY-4-THIO-D-ERYTHRO-PENTOFURANOSE DERIVATIVES, Journal of the Chemical Society. Perkin transactions. I, (14), 1996, pp. 1665-1671
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
14
Year of publication
1996
Pages
1665 - 1671
Database
ISI
SICI code
0300-922X(1996):14<1665:SACAO3>2.0.ZU;2-C
Abstract
A new route is described to -2-deoxy-4-thio-alpha,beta-D-erythro-pento furanose derivatives starting from L-arabinose. This route is amenable to variation in the 3-substituent and the 3-O-benzoyl and 3-azido der ivatives were obtained in 17 and 15% yields, respectively, making this procedure easily the most economical entry to 4'-thionucleosides. The anomeric configuration of these and other thiosugars is established u nequivocally.