Journal article
Syntheses and structure assignments of six azolinone ribonucleosides
Journal of organic chemistry, Vol.47(3), pp.474-482
01/01/1982
DOI: 10.1021/jo00342a020
Abstract
N-Ribosidation of a series of azolinones was achieved via silylation and SnCl4 catalysis. N-Ribosidation of 4-imidazolin-2-one gave l-β-d-ribofuranosyl-4-imidazolin-2-one; of 1,2,4-triazolin-3-one gave 2- and 4-β-d-ribo-furanosyl-1,2,4-triazolin-3-one, and 2,4-di-β-d-ribofuranosyl-1,2,4-triazolin-3-one; and of 2-tetrazolin-5-one gave 1-β-d-ribofuranosyl-2-tetrazolin-5-one and 1,4-di-β-d-ribofuranosyl-2-tetrazolin-5-one. Structure assignments were based on NMR and mass spectra, microanalytical data, and interconversions. The triazolinone monoriboside isomer structures were differentiated by 13C NMR long-range coupling patterns, and the assignments were confirmed by X-ray crystallography. New syntheses were developed for several of the ribonucleosides by fashioning the azolinone rings from 2,3,5-tri-O-benzoyIribofuranosyl isocyanate. © 1982, American Chemical Society. All rights reserved.
Details
- Title: Subtitle
- Syntheses and structure assignments of six azolinone ribonucleosides
- Creators
- David R HainesNelson J LeonardDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.47(3), pp.474-482
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00342a020
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 01/01/1982
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9984216672002771
Metrics
8 Record Views