Journal of Organic Chemistry p. 4265 - 4268 (1982)
Update date:2022-08-04
Topics:
Mubarak, Azeez
Fraser-Reid, Bert
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.
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