Abstract
The xylitol, ribitol and D-arabinitol were transformed into their tributylstannyl ether derivatives by reaction with bis-tributyltin oxide [(nBu3Sn)2O I] and azeotropic removal of water. Subsequent benzyl etherification, using BnBr with solvent or under free solvent conditions, led regioselectively to primary mono-O-benzylalditol derivatives in satisfactory yields for a direct regioselective synthesis (∼ 52%). This etherification when applied to tetritols and some hexitols exhibits similar behaviour. With pentitols, an analogous study carried out with the n-dibutyltin oxide [nBu2SnO (II)] as the activating reagent showed contrasting results as regards regioselectivity.
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