Formation of glycosides by epoxidation-ring closure of open-chain hydroxyenol ethers obtained from sugars

Francesco Nicotra, Luigi Panza, Fiamma Ronchetti, Giovanni Russo, Lucio Toma

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

Z- and E-Hydroxyenol ethers, obtained from aldopentoses by a Horner-Wittig reaction, have been epoxidized using m-chloroperbenzoic acid or t-butyl hydroperoxide. A spontaneous intramolecular cyclization of the intermediate epoxides due to the free hydroxy group present in the starting enol ethers occurs, giving 1,2-trans-glycopyranosides from E-enol ethers. From Z-enol ethers, 1,2-cis-glycopyranosides are obtained, although in the case of complex aglycones the cyclization is not entirely stereospecific. The stereochemical course of both the epoxidation reaction and the pyranose ring formation from the intermediate epoxides is discussed.

Lingua originaleInglese
pagine (da-a)1319-1324
Numero di pagine6
RivistaJournal of the Chemical Society, Perkin Transactions 1
DOI
Stato di pubblicazionePubblicato - 1987
Pubblicato esternamente

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