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- W2335769920 abstract "A systematic study of the suitability of α,α′-dibromo-o-xylene as a reagent for cyclic o-xylylene protection of vic-diols in different monosaccharide substrates is reported. The installation of this protecting group, formally equivalent to a di-O-benzylation reaction, proceeds with good regioselectivity toward 1,2-trans-diequatorial diol systems in pyranose and furanose rings. Initially, the benzyl ether-type derivative of the more acidic hydroxyl is preferentially formed. Subsequent intramolecular etherification toward the equatorial-oriented vicinal OH is kinetically favored. The methodology has been implemented for the simultaneous protection of the secondary O-2 and O-3 positions of a single d-glucopyranosyl unit in cyclic oligosaccharides of the cyclodextrin (CD) family (cyclomaltohexa-, -hepta-, and -octaose; α, β, and γCD)." @default.
- W2335769920 created "2016-06-24" @default.
- W2335769920 creator A5025899580 @default.
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- W2335769920 creator A5071030408 @default.
- W2335769920 creator A5082081763 @default.
- W2335769920 date "2013-02-04" @default.
- W2335769920 modified "2023-10-11" @default.
- W2335769920 title "<i>o</i>-Xylylene Protecting Group in Carbohydrate Chemistry: Application to the Regioselective Protection of a Single <i>vic</i>-Diol Segment in Cyclodextrins" @default.
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- W2335769920 doi "https://doi.org/10.1021/jo302178f" @default.
- W2335769920 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23336396" @default.
- W2335769920 hasPublicationYear "2013" @default.
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