A1 Journal article (refereed)
Improved synthesis and application of conjugation-amenable polyols from d-mannose (2020)


Mattsson, I., Sitdikov, R., Gunell, A. C. M., Lahtinen, M., Saloranta-Simell, T., & Leino, R. (2020). Improved synthesis and application of conjugation-amenable polyols from d-mannose. RSC Advances, 10(7), 3960-3966. https://doi.org/10.1039/c9ra10378c


JYU authors or editors


Publication details

All authors or editorsMattsson, Ida; Sitdikov, Ruzal; Gunell, Andreas C. M.; Lahtinen, Manu; Saloranta-Simell, Tiina; Leino, Reko

Journal or seriesRSC Advances

eISSN2046-2069

Publication year2020

Volume10

Issue number7

Pages range3960-3966

PublisherRoyal Society of Chemistry

Publication countryUnited Kingdom

Publication languageEnglish

DOIhttps://doi.org/10.1039/c9ra10378c

Publication open accessOpenly available

Publication channel open accessOpen Access channel

Publication is parallel published (JYX)https://jyx.jyu.fi/handle/123456789/67576


Abstract

A series of polyhydroxyl sulfides and triazoles was prepared by reacting allyl and propargyl D-mannose derivatives with selected thiols and azides in thiol–ene and Huisgen click reactions. Conformational analysis by NMR spectroscopy proved that the intrinsic rigidity and linear conformation of the mannose derived polyol backbone is retained in the final click products in solution. Single crystal X-ray structure determination of one of the compounds prepared further verified that the linear conformation of the polyol segment is also retained in the solid state. In addition, an improved method for direct Barbier-type propargylation of unprotected D-mannose is reported. The new reaction protocol, involving tin-mediated propargylation in an acetonitrile-water mixture, provides access to multigram quantities of the desired, valuable alkyne polyol without relying on protecting group manipulations or chromatographic purification.


Keywordschemical synthesissugar alcohols

Free keywordssynthesis


Contributing organizations


Ministry reportingYes

Reporting Year2020

JUFO rating1


Last updated on 2024-22-04 at 13:30