STEREOSELECTIVE SYNTHESIS OF α-RIBONUCLEOSIDES FROM 1-HYDROXY SUGARS BY USING 2-FLUOROPYRIDINIUM TOSYLATE
- 5 April 1984
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 13 (4) , 557-560
- https://doi.org/10.1246/cl.1984.557
Abstract
A novel method for the preparation of α-ribonucleosides was developed by the use of 2-fluoro-1-methylpyridinium tosylate as a condensing reagent. Various α-ribonucleosides were synthesized from 1-hydroxy sugars and trimethylsilylated nitrogen compounds, such as nucleoside bases and azide, in good yields under mild conditions.Keywords
This publication has 10 references indexed in Scilit:
- d-ribofuranosyl azides. A direct conversion of 1-O-acyl-2,3-O-isopropylidene-d-ribofuranose into d-ribofuranosyl azidesCarbohydrate Research, 1983
- 2-Amino-7-(.beta.-D-arabinofuranosyl)pyrrolo[2,3-d]pyrimidin-4(3H)-one. Synthesis of ara-7-deazaguanosine via phase-transfer glycosylationThe Journal of Organic Chemistry, 1982
- 2,3,5-tri-O-acety]-β-D-ribofuranosyl azide and 2,3-O-isopropylidene-5-O-trityl-α-D-ribofuranosyl azideCarbohydrate Research, 1980
- Synthesis of certain .beta.-D-ribofuranosyl thiazole C-nucleosides from a versatile precursorThe Journal of Organic Chemistry, 1979
- New Synthetic Reactions Based on the Onium Salts of Aza‐Arenes [New synthetic methods (29)]Angewandte Chemie International Edition in English, 1979
- A new aspect of the use of 2′,3′-O-isopropylidene ribonucleosides for investigation of anomeric configurationCarbohydrate Research, 1977
- Studies on the Δδ criterion for determining the anomeric configuration of ribofuranosyl nucleosidesCarbohydrate Research, 1976
- Synthesis with partially benzylated sugars. XI. Synthesis of the anomeric 5,6-dimethyl-1-D-ribofuranosylbenz-imidazoles (ribazoles). Comparison of the condensation of 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide and 2,3,5-O benzyl-D-ribofuranosyl chloride with 5,6-dimethylbenzimidazoleThe Journal of Organic Chemistry, 1968
- Studies on Synthetic Nucleosides V. Anomeric Pyrimidine Nucleosides of D-Arabinose and D-LyxoseCHEMICAL & PHARMACEUTICAL BULLETIN, 1965
- 2,3,5-Tri-O-benzyl-D-ribosyl and -L-arabinosyl BromidesThe Journal of Organic Chemistry, 1961