PHOTOLYSIS OF METHYL 1-AZIDO GLUCOSIDES - UNPRECEDENTED EXPANSIONS OFTHE PYRANOSE RING UNDER HIGH STEREOCONTROL

Authors
DISTEFANO C DESCOTES G PRALY JP
Citation
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
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
1
Year of publication
1994
Pages
93 - 96
Database
ISI
SICI code
0040-4039(1994)35:1<93:POM1G->2.0.ZU;2-A
Abstract
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.