Carbohydrate Research 2003-10-10

Neighboring-group participation in benzylidene acetal ring-opening of a 2-cyano-2-deoxypyranoside derivative by diethylaluminum cyanide.

María I Mangione, Alejandra G Suárez, Rolando A Spanevello

Index: Carbohydr. Res. 338 , 2177-83, (2003)

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Abstract

The oxirane ring-opening of an anhydro sugar with diethylaluminum cyanide (Et(2)AlCN) is a direct approach for obtaining a cyano derivative. Methyl 2,3-anhydro-4,6-O-benzylidene-alpha-D-allopyranoside showed anomalous chemical behavior when treated with Et(2)AlCN. The reaction afforded the corresponding beta-cyanohydrin as the minor component from a mixture of compounds resulting from the benzylidene acetal ring-opening caused by the attack of ethyl or cyano groups.