Year: 1979
Type: article
Abstract: Reaction of 3,4,6-tri-O-acetyl-D-galactal with excess ceric ammonium nitrate and sodium azide in acetonitrile produced 2-azido-1-nitrate addition products (53% β-galacto, 22% α-galacto, and 8% α-talo) and N-acetyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosylamine was formed, on hydrolysis, in 10% yield. The reaction product provides a convenient source of D-galactosamine and 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosylhalides. The crystalline β-chloride is also reported. The use of these glycosyl halides as reactants for the preparation of 2-azido-2-deoxy-α- and -β-D-galactopyranosides under conditions promoted by both mercuric cyanide and silver salts are reported.
Source: Canadian Journal of Chemistry
DOI: 10.1139/v79-203
Authors: R. U. Lemieux, R. M. Ratcliffe
Institutions: University of Alberta, National Research Council Canada
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
Funder: University of Alberta
OpenAlex ID: W1964316590