Stereoselective O-glycosylation of trans-4-hydroxy-L-proline derivatives promoted by silver zeolite.
Trans-4-hydroxy-L-proline has been converted to four imino- and carboxyl-blocked derivatives which are suitable for the synthesis of 4-O-glycosyl conjugates. Reaction of these derivatives with 2,3,5-tri-O-benzyl-alpha-L-arabinofuranosyl chloride in the presence of a silver zeolite promoter yielded the blocked beta-furanosyl amino-acid conjugates. Deprotection gave trans-4-(beta-L-arabinofuranosyloxy)-L-proline which was characterised as its crystalline isopropyl ester. 13C-NMR Data are presented for the compounds described.
Finch
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Bourne Laboratory, Royal Holloway and Bedford New College, Egham, Surrey, England.
Siriwardena
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D000538:Aluminum Silicates; D001089:Arabinose; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006909:Hydroxyproline; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D012834:Silver; D013237:Stereoisomerism; D017641:Zeolites
D000538:Aluminum Silicates; D006001:Glycoconjugates; D007202:Indicators and Reagents; D017641:Zeolites; D012834:Silver; D001089:Arabinose; D006909:Hydroxyproline