Synthesis of sugar-lactams from azides of glucuronic acid.
Sugar-lactams have found application as glycosidase inhibitors, synthetic precursors of iminosugars and they are structural components of natural products. The synthesis of beta-D-glucopyranosidurono-6,1-lactams from glucuronic acid derivatives are described. NMR data and X-ray crystal structures indicate that the sugar-lactams adopt distorted (1)C4 conformations in solution and in the solid state.
Loukou
Christina
C
UCD School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, UCD Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland.
Tosin
Manuela
M
Müller-Bunz
Helge
H
Murphy
Paul V
PV
D001386:Azides; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry; D020723:Glucuronic Acid / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular
D001386:Azides; D002241:Carbohydrates; D005960:Glucosides; D007769:Lactams; D020723:Glucuronic Acid