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Selective cleavage of methoxy protecting groups in carbohydrates

AuthorsBoto, Alicia ; Hernández, Dácil ; Hernández, Rosendo ; Suárez, Ernesto
Issue Date28-Jan-2006
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 71: 1938-1948 (2006)
AbstractThe selective cleavage of methoxy protecting groups next to hydroxy groups is achieved using a radical hydrogen abstraction reaction as the key step. Under the reaction conditions, the hydroxy group generates an alkoxyl radical that reacts with the sterically accessible adjacent methoxy group, which is transformed into an acetal. In the second step, the acetals are hydrolyzed to give alcohols or diols. A one-pot hydrogen abstraction−hydrolysis procedure was also developed. Good yields were usually achieved, and the mild conditions of this methodology were compatible with different functional groups and sensitive substrates such as carbohydrates.
Description11 pages, 1 figure, 1 table, 16 schemes.-- PMID: 16496979 [PubMed].-- Printed version published Mar 3, 2006.
Supporting information available: General procedures and synthesis of IHA substrates 5-9 and 12-15. Spectroscopic data for compounds 13, 17 and 18, 20 and 21, 23-26, and 33, and the 1H and 13C NMR spectra for the new IHA or hydrolysis products (compounds 34-46, 48-52, 54-55, 57-62).-- Available at: http://pubs.acs.org/doi/suppl/10.1021/jo052313o
Publisher version (URL)http://dx.doi.org/10.1021/jo052313o
Appears in Collections:(IPNA) Artículos
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