Synthesis 2017; 49(24): 5320-5334
DOI: 10.1055/s-0036-1591518
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1,5-Anhydro-d-glycero-d-gluco-heptitol Derivatives as Potential Inhibitors of Bacterial Heptose Biosynthetic Pathways

Markus Blaukopf
University of Natural Resources and Life Sciences-Vienna, Department of Chemistry, Muthgasse 18, 1190 Vienna, Austria
,
Dmytro Atamanyuk
Mutabilis, Avenue Gaston Roussel, 93230 Romainville, France   Email: paul.kosma@boku.ac.at
,
Nuno M. Xavier
University of Natural Resources and Life Sciences-Vienna, Department of Chemistry, Muthgasse 18, 1190 Vienna, Austria
,
Vincent Gerusz
Mutabilis, Avenue Gaston Roussel, 93230 Romainville, France   Email: paul.kosma@boku.ac.at
,
University of Natural Resources and Life Sciences-Vienna, Department of Chemistry, Muthgasse 18, 1190 Vienna, Austria
› Author Affiliations
Further Information

Publication History

Received: 01 September 2017

Accepted after revision: 12 October 2017

Publication Date:
08 November 2017 (eFirst)

Abstract

A series of 1,5-anhydro-d-glycero-d-gluco-heptitol derivatives have been prepared from 3-O-benzyl-1,2-O-isopropylidene-d-glycero-d-gluco-heptofuranose via conversion into anomeric bromide and thiophenyl derivatives, followed by glycal formation and reductive desulfurization, respectively. Global deprotection of the protected intermediates afforded the 1,5-anhydro derivatives of the d-glycero-d-gluco- and 1,2-dideoxy-d-altro- configuration as well as the 1,5-anhydro-2-deoxy-d-altro-hept-1-enitol. In addition, the 7-O-phosphorylated d-glycero-d-gluco-heptose and its 1,5-anhydro analogue were prepared in good yields utilizing phosphoramidite chemistry. A novel heptitol analogue based on a 1-deoxynojirimycin scaffold was also elaborated via a Wittig­-type chain elongation followed by dihydroxylation, separation of the resulting epimers, and global deprotection. The target compounds, however, were not active as inhibitors of the bacterial sedoheptulose-7-phosphate isomerase GmhA.

Supporting Information

 
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