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A series of d-mannopyranosyl and l-rhamnopyranosyl thioglycosides protected with electron-withdrawing, non-participating protecting groups on O-2 have been prepared and investigated for their potential as β-glycosyl donors. Both α- and β-thioglycosides were investigated and the latter preferred on the grounds of enhanced stability at room temperature. A 2-O-nitro-l-rhamnosyl fluoride was also prepared...
Diastereomeric 3-O-allyl-4,6-O-benzylidene-2-O-(diphenylphosphatoxy) β-d-gluco- and β-d-manno-pyranosyl phenylselenides were prepared and subjected to treatment with tributyltin hydride and AIBN. The gluco-compound undergoes smooth radical cyclization to a single diastereomeric product in high yield whereas the manno-isomer reacts only reluctantly to give a complex mixture. This difference in behavior...
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