Conformations of methyl 2,5-di-O-acetyl-beta-D-glucofuranosidurono-6,3-lactone and 1,2,5-tri-O-acetyl-beta-D-glucofuranurono-6,3-lactone in the crystal structure and in solution.
The single-crystal X-ray diffraction and high-resolution 1H and 13C NMR spectral data for methyl 2,5-di-O-acetyl-beta-D-glucofuranosidurono-6,3-lactone and 1,2,5-tri-O-acetyl-beta-D-glucofuranurono-6,3-lactone are reported. The lactones were synthesized as byproducts of reactions carried out to obtain methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate. The conformations of these lactones in the crystal structure and in solution are discussed. A 1T2-like conformation was found to be the preferred form for these lactones in both the crystal lattice and in solution.
Liberek
Beata
B
Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, PL-80-952 Gdańsk, Poland. beatal@chem.univ.gda.pl
Tuwalska
Dorota
D
Santos-Zounon
Iwona do
Id
Konitz
Antoni
A
Sikorski
Artur
A
Smiatacz
Zygfryd
Z
D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D012996:Solutions / Q000737:chemistry
C513755:1,2,5-tri-O-acetylglucofuranosidurono-6,3-lactone; D005960:Glucosides; D007783:Lactones; D009844:Oligosaccharides; D012996:Solutions; C513754:methyl 2,5-di-O-acetylglucofuranosidurono-6,3-lactone; C439623:1,2,3,4-tetra-O-acetylglucopyranose