Neighboring-group participation in benzylidene acetal ring-opening of a 2-cyano-2-deoxypyranoside derivative by diethylaluminum cyanide.
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.
Mangione
María I
MI
Instituto de Química Orgánica de Síntesis, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina.
Suárez
Alejandra G
AG
Spanevello
Rolando A
RA
D001597:Benzylidene Compounds / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*
D001597:Benzylidene Compounds; D006027:Glycosides; D009942:Organometallic Compounds; D011714:Pyrans; C488013:diethylaluminum cyanide