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Fragmentation of carbohydrate anomeric alkoxyl radicals. Synthesis of highly functionalized chiral vinyl sulfones

AuthorsAlonso-Cruz, Carmen R. ; León, Elisa I. ; Ortiz-López, Francisco J.; Rodríguez Morales, María S. ; Suárez, Ernesto
Issue Date1-Jul-2005
CitationTetrahedron Letters 46(32): 5265-5268 (2005)
AbstractThe reaction of derivatives of 3-acetyl-d-glucal, 3-acetyl-l-rhamnal, 3-acetyl-d-galactal, and 3-acetyl-d-lactal with sodium benzenesulfinate in acid medium catalyzed by HgSO4 afforded diastereoisomeric mixtures of the corresponding 2,3-dideoxy-3-(phenylsulfonyl)-hexopyranoses through a Ferrier rearrangement. The anomeric alkoxyl radical fragmentation of these γ-hydroxy sulfones using the system (diacetoxyiodo)benzene and iodine gave vinyl sulfones with structures of 1,2-dideoxy-4-O-formyl-2-(phenylsulfonyl)-pent-1-enitol and configurations d-erythro, l-erythro, and d-threo at the two stereogenic centers.
Description4 pages, 1 table, 1 scheme.-- Printed version published Aug 8, 2005.-- Corrigendum published in Tetrahedron Letters 47(8): 1359 (Feb 2006), http://dx.doi.org/10.1016/j.tetlet.2005.12.035
Supporting information (6 page Word file) available at: http://dx.doi.org/10.1016/j.tetlet.2005.06.043
Publisher version (URL)http://dx.doi.org/10.1016/j.tetlet.2005.06.043
Appears in Collections:(IPNA) Artículos
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