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Monosaccharides as Potential Chiral Probes for the Determination of the Absolute Configuration of Secondary Alcohols
Abstract
Herein, a new method for the elucidation of the absolute configuration of chiral secondary alcohols is proposed. This method is an alternative for a widely used approach reported by Mosher and Dale and similar methods that are based on the 1H NMR shift (δ) changes of protons that are attached to the substituents of the oxymethine carbon atom. The presented method is not based on tracking the chemical shift changes and utilizes stereochemically defined monosaccharides as chiral probes. A secondary alcohol is glycosylated, and the resulting glycoside is subjected to NMR studies. The observation of dipolar couplings between the protons of the monosaccharide moiety and the protons of the secondary alcohol moiety via the NOESY/ROESY spectra enables the determination of the absolute configuration of the oxymethine carbon atom.
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
JOURNAL OF NATURAL PRODUCTS
no. 79,
edition 11,
pages 2797 - 2804,
ISSN: 0163-3864 - Language:
- English
- Publication year:
- 2016
- Bibliographic description:
- Laskowski T., Szwarc K., Szczeblewski P., Sowiński P., Borowski E., Pawlak J.: Monosaccharides as Potential Chiral Probes for the Determination of the Absolute Configuration of Secondary Alcohols// JOURNAL OF NATURAL PRODUCTS. -Vol. 79, iss. 11 (2016), s.2797-2804
- DOI:
- Digital Object Identifier (open in new tab) 10.1021/acs.jnatprod.6b00471
- Verified by:
- Gdańsk University of Technology
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