Guo H, O'Doherty GA De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide Journal of Organic Chemistry73(14) (2008)
5211-5220
The structure was elucidated in this paper NCBI PubMed ID:18563936 Journal NLM ID:2985193R Publisher: Columbus, OH: American Chemical Society Correspondence: george.odohertymail.wVu.edu Institutions: Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA
A de novo asymmetric approach to the natural product anthrax tetrasaccharide 1 and an analogue 2 with an anomeric hexyl azide group has been developed from acetylfuran. The construction of the tetrasaccharide was achieved by a traditional [3 + 1] glycosylation strategy. An iterative diastereoselective palladium-catalyzed glycosylation, Luche reduction, diastereoselective dihydroxylation, and regioselective acylation were employed for the assembly of the L-rhamno-trisaccharide building block. The anthrose building block also required a palladium-catalyzed azide allylation and a triflate inversion to set the gluco-stereochemistry in addition to Luche reduction and dihydroxylation
Methods: 13C NMR, 1H NMR, NMR-2D, chemical synthesis Synthetic data: chemical Comments, role: Azide anthrax tetrasaccharide 2 was synthesized.
Related record ID(s): 10613, 22680, 23501 NCBI Taxonomy refs (TaxIDs):1392 Reference(s) to other database(s): GlycomeDB:27777 Show glycosyltransferases
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