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Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons

AuthorsFrancisco, Cosme G. ; León, Elisa I. ; Martín, Ángeles ; Moreno, Pilar ; Rodríguez Morales, María S. ; Suárez, Ernesto
Issue Date18-Sep-2001
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 66(21): 6967-6976 (2001)
AbstractA series of anomeric nitrate esters and N-phthalimido glycosides of carbohydrates in furanose and pyranose forms have been synthesized in order to generate the corresponding alkoxy radicals and study the C1−C2 fragmentation reaction under reductive conditions. This reaction constitutes a two-step method for the transformation of carbohydrates into the corresponding alditols with one less carbon. Using this methodology, interesting four- and five-carbon building blocks for natural products synthesis possessing d-erythritol, d-threitol, d-xylitol, and d-arabinitol stereochemistry have been prepared. The synthesis of 1,2-O-isopropylidene-β-l-threose (40) and 1-acetamido-2,4,5-tri-O-acetyl-d-arabinitol (50) have also been achieved from 1,2:5,6-di-O-isopropylidene-β-d-glucofuranose and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-d-glucopyranose, respectively.
Description10 pages, 3 tables, 3 schemes.-- PMID: 11597215 [PubMed].-- Printed version published Oct 19, 2001.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo0156565
Publisher version (URL)http://dx.doi.org/10.1021/jo0156565
Appears in Collections:(IPNA) Artículos
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