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Lewis acid catalyzed isomerization of benzylidene acetals of methyl alpha l rhamno pyranoside and methyl beta l arabino pyranoside derivatives



Lewis acid catalyzed isomerization of benzylidene acetals of methyl alpha l rhamno pyranoside and methyl beta l arabino pyranoside derivatives



Carbohydrate Research 98(2): 165-172



The Lewis-acid-catalyzed isomerization of several derivatives of methyl 2,3-O-benzylidene-.alpha.-L-rhamnopyranoside and methyl 3,4-O-benzylidene-.beta.-L-arabinopyranoside was investigated. The presence of equatorial substituents vicinal to the benzylidene ring decreases the rate of isomerization, and exo isomers isomerize more quickly than the corresponding endo isomers. The occurrence of isomerization during the reductive cleavage reaction of acetal rings with LiAlH4-AlCl3 was demonstrated.

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Accession: 005806556

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