Picture of aircraft jet engine

Strathclyde research that powers aerospace engineering...

The Strathprints institutional repository is a digital archive of University of Strathclyde's Open Access research outputs. Strathprints provides access to thousands of Open Access research papers by University of Strathclyde researchers, including by Strathclyde researchers involved in aerospace engineering and from the Advanced Space Concepts Laboratory - but also other internationally significant research from within the Department of Mechanical & Aerospace Engineering. Discover why Strathclyde is powering international aerospace research...

Strathprints also exposes world leading research from the Faculties of Science, Engineering, Humanities & Social Sciences, and from the Strathclyde Business School.

Discover more...

Total syntheses of conformationally-locked difluorinated pentopyranose analogues and a pentopyranosyl phosphate mimetic

Percy, J.M. and Mitchell, L. and Singh, K. and Uneyama, E. and Miles, J.A.L. (2007) Total syntheses of conformationally-locked difluorinated pentopyranose analogues and a pentopyranosyl phosphate mimetic. Journal of Organic Chemistry, 72. pp. 1575-1587. ISSN 0022-3263

[img]
Preview
PDF
329602.pdf - Final Published Version

Download (302kB) | Preview

Abstract

Trifluoroethanol has been elaborated, via a telescoped sequence involving a metalated difluoroenol, a difluoroallylic alcohol, [2,3]-Wittig rearrangement, and ultimately an RCM reaction and requiring minimal intermediate purification, to a number of cyclooctenone intermediates. Epoxidation of these intermediates followed by transannular ring opening or dihydroxylation, then transannular hemiacetalization delivers novel bicyclic analogues of pentopyranoses, which were elaborated (in one case) to an analogue of a glycosyl phosphate.