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• W2097637360 endingPage "10381" @default.
• W2097637360 startingPage "10369" @default.
• W2097637360 abstract "Abstract The stereochemical and conformational factors controlling the intramolecular hydrogen‐atom transfer (HAT) reaction between the two pyranose units in a (1→4)‐ O ‐disaccharide when promoted by a primary 6‐ O ‐yl radical are studied. Models with α‐ D ‐Glc p ‐(1→4)‐β‐ D ‐Glc p , α‐ L ‐Rham p ‐(1→4)‐α‐ D ‐Gal p or α‐ D ‐Man p ‐(1→4)‐β‐ L ‐Gul p skeletons led exclusively to the abstraction of the hydrogen from HC‐5′ and the formation, through a nine‐membered transition state, of a 1,3,5‐trioxocane ring system in a stable boat–chair conformation. Notwithstanding, derivatives of α‐ L ‐Rham p ‐(1→4)‐α‐ D ‐Glc p or α‐ D ‐Man p ‐(1→4)‐α‐ D ‐Gal p exclusively abstract the hydrogen from HC‐1′ through a seven‐membered transition state and, therefore, lead to an interglycosidic spiro ortho ester." @default.
• W2097637360 created "2016-06-24" @default.
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• W2097637360 creator A5061269162 @default.
• W2097637360 creator A5085251865 @default.
• W2097637360 date "2008-11-10" @default.
• W2097637360 modified "2023-10-18" @default.
• W2097637360 title "Intramolecular 1,8-Hydrogen-Atom Transfer Reactions in (1→4)-<i>O</i>-Disaccharide Systems: Conformational and Stereochemical Requirements" @default.
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• W2097637360 doi "https://doi.org/10.1002/chem.200801414" @default.
• W2097637360 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/18830990" @default.
• W2097637360 hasPublicationYear "2008" @default.
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