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Title

Free-Radical Epimerization of D- into L-C-(glycosyl)methanol Compounds Using 1,5-Hydrogen Atom Transfer Reaction

AuthorsMontes, Adrián S.; León, Elisa I. CSIC ORCID ; Martín, Ángeles CSIC ORCID ; Pérez-Martín, Inés CSIC ORCID ; Suárez, Ernesto CSIC ORCID
KeywordsC-Glycosides
C-H activation
Hydrogen transfer
Radical reactions
Regioselectivity
Issue Date18-Jan-2022
PublisherJohn Wiley & Sons
CitationEuropean Journal of Organic Chemistry, 2022(16) : 1-27 (2022)
AbstractA simple epimerization of C-(α-D-Gly p )methanol into C-(β-L-Gly p )methanol compounds is described. The radical sequence involved homolytic cleavage of the C5–H bond by 1,5-hydrogen atom transfer promoted by the 1’-O-yl radical and subsequent hydride addition with inversion of configuration. This methodology allows the preparation of rare C-(β-L-Ido p )-, C-(β-L-Altp)-, C-(β-L-Gulp)-, C-(β-L-Allp)methanol glycosides starting from carbohydrates of the D-series. It can also be applied to transform L- into D-configured C-glycosyl compounds, as illustrated by the formation of C-(β-D-6dGulp)- and C-(β-D-6dAltp)methanol from readily accessible L-rhamno and L-fuco analogs, respectively. In further development of this procedure compounds with C-(β-L-Araf)- and C-(β-L-5dRibf)methanol structures have also been synthesized. The alkoxyl radicals were generated by reaction of the corresponding N-alkoxyphthalimides with nBu3SnH(D) and in comparative terms, by visible light-photocatalysis using the Hantzsch ester/fac-Ir(ppy)3 procedure. The influence of the sugar ring conformation and the electronegativity of the substituents on the stereochemical outcome will be addressed.
Publisher version (URL)https://doi.org/10.1002/ejoc.202101391
URIhttp://hdl.handle.net/10261/258275
DOI10.1002/ejoc.202101391
ISSN1434-193X
E-ISSN1099-0690
Appears in Collections:(IPNA) Artículos




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