The Anomeric Pudovik Rearrangement.
The O,O-dibenzyl-S-glycosyl phosphothioite derived from 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-alpha-D-glucopyranose rearranges under the influence of triethylborane and air to provide the corresponding 1-C-pyranosyl-O,O-dibenzylphosphonothioate, a new type of carbohydrate derivative. The isomeric beta phosphothioite is compared, and evidence of a radical chain mechanism for the Pudovik rearrangement is presented.
Knapp
Spencer
S
Department of Chemistry & Chemical Biology, Rutgers - The State University of New Jersey 610 Taylor Road, Piscataway, New Jersey 08854-8087 USA.
Ajayi
Kehinde
K