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Synthesis of highly condensed polycyclic carbohydrates by reaction of a spirocyclic enamino sulfonate derived from d-xylofuranose with bifunctional reagents.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2007 Dec 07; Vol. 72 (25), pp. 9713-21. Date of Electronic Publication: 2007 Nov 14. - Publication Year :
- 2007
-
Abstract
- The appropriately substituted 5-O-tosyl derivative (1), easily prepared from 1,2-O-isopropylidene-alpha-d-xylofuranose, serves as a useful precursor for the preparation of highly condensed cyclic carbohydrates. The synthesis involves a first cyclization of the 5-O-tosyl sugar derivative 1 to a highly reactive cyclic enamine, which subsequently undergoes the nucleophilic attack of a bifunctional reagent X(CH2)nZ in a regio- and stereospecific way. Finally, a spontaneous cyclization step allows the formation of a stereochemically defined extra ring, fused to the sugar backbone. The functionalization and size of this ring can be varied by the proper choice of the bifunctional reagent. X-ray diffraction analysis and intensive NMR studies with one of these carbohydrates were performed to highlight the strained nature of these compounds.
- Subjects :
- Alkanesulfonates chemical synthesis
Carbohydrates chemistry
Crystallography, X-Ray
Magnetic Resonance Spectroscopy methods
Magnetic Resonance Spectroscopy standards
Models, Molecular
Molecular Conformation
Reference Standards
Spiro Compounds chemical synthesis
Stereoisomerism
Alkanesulfonates chemistry
Carbohydrates chemical synthesis
Indicators and Reagents chemistry
Spiro Compounds chemistry
Xylose analogs & derivatives
Xylose chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 0022-3263
- Volume :
- 72
- Issue :
- 25
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 17999530
- Full Text :
- https://doi.org/10.1021/jo701775a