Synthethic Routes to 3-C-Cyano-3-deoxy-D-galactopyranose Derivatives

Article abstract of DOI:10.1021/jo00143a018

Routes to 3-C-cyano-3-deoxy-D-galactopyranose derivatives have been developed from methyl 3,4-anhydro-α-D-galactopyranoside and 1,6:3,4-dianhydro-β-D-galactopyranose.Upon treatment with diethylaluminum cyanide, both precursors give products of trans-diaxial opening although some diequatorial opening also occurs with the former.The axial C-cyano groups in both cases are readily epimerized by dilute sodium methoxide, giving 3-C-cyano-3-deoxy-D-galacto products.In neither case is there any evidence of β elimination or of skeletal rearrangements.