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 editors: Mattsson, Ida; Sitdikov, Ruzal; Gunell, Andreas C. M.; Lahtinen, Manu; Saloranta-Simell, Tiina; Leino, Reko

Journal or series: RSC Advances

eISSN: 2046-2069

Publication year: 2020

Volume: 10

Issue number: 7

Pages range: 3960-3966

Publisher: Royal Society of Chemistry

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/c9ra10378c

Publication open access: Openly available

Publication channel open access: Open 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.

Keywords: chemical synthesis; sugar alcohols

Free keywords: synthesis

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2020

JUFO rating: 1