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- W2950723825 abstract "Abstract Acid-catalysed opening of five- and six-membered cyclic orthoesters of hexopyranosides is well explored and often used in synthetic pathways.1-7 Opening of a five-membered ring orthoacetate or benzoate (formed from cis-vic-diols) gives the axial ester,1,2 contrary to most other regioselective methods which give preferentially the equatorial ester, whereas opening of six-membered ring 4,6-orthoesters give a mixture of 4- and 6-esters, the ratio depending in part on the substituent at O-3 and on the amount of acyl migration during the reaction conditions.3,4 Since chlorinated acetates (mono-, di- and tri-) are selectively removable in the presence of acetates and benzoates,8 their introduction by means of the acidic opening of the corresponding orthoacetate could give a route to a flexible protecting group scheme with regioselective introduction of the selectively removable chloroacetate. This would open up a suitable way for synthesis of, inter alia, branched oligosaccharides. Therefore, mono-, di..." @default.
- W2950723825 created "2019-06-27" @default.
- W2950723825 creator A5058877795 @default.
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- W2950723825 date "2010-08-04" @default.
- W2950723825 modified "2023-09-26" @default.
- W2950723825 title "ChemInform Abstract: Synthesis and Acidic Opening of Chlorinated Carbohydrate Orthoacetates." @default.
- W2950723825 cites W2026962591 @default.
- W2950723825 doi "https://doi.org/10.1002/chin.199643195" @default.
- W2950723825 hasPublicationYear "2010" @default.
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