TY - JOUR
T1 - Formation of glycosides by epoxidation-ring closure of open-chain hydroxyenol ethers obtained from sugars
AU - Nicotra, Francesco
AU - Panza, Luigi
AU - Ronchetti, Fiamma
AU - Russo, Giovanni
AU - Toma, Lucio
PY - 1987
Y1 - 1987
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=37049086239&partnerID=8YFLogxK
U2 - 10.1039/p19870001319
DO - 10.1039/p19870001319
M3 - Article
SN - 1472-7781
SP - 1319
EP - 1324
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -