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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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