C. Distefano et al., PHOTOLYSIS OF METHYL 1-AZIDO GLUCOSIDES - UNPRECEDENTED EXPANSIONS OFTHE PYRANOSE RING UNDER HIGH STEREOCONTROL, Tetrahedron letters, 35(1), 1994, pp. 93-96
New structures arising from the photolysis of peracetylated methyl 1-a
zido-D-glucopyranosides account for the formation of excited intermedi
ates which undergo stereocontrolled migrations of either the O-5 oxyge
n atom (a) or, competitively, the O-1 oxygen atom (b) or the C-2 carbo
n atom (c), depending, respectively, on the alpha or beta orientation
or the azido group in the substrate.