Acid-catalyzed isomerization of methyl 2-deoxy-D-arabino-hexosides: equilibria, kinetics and mechanism.
Four isomers of methyl 2-deoxy-D-arabino-hexosides were isolated by HPLC as chromatographically homogeneous compounds. The rates of pyranoside isomerization (alpha(p) and beta(p)) at 40 degrees C and of furanoside isomerization (alpha(f) and beta(f)) at 26 degrees C were determined. A mechanism has been suggested for transformations taking place during isomerization of methyl 2-deoxy-D-arabino-hexosides in methanolic solution catalyzed with hydrogen chloride.
Nowacki
Andrzej
A
Department of Chemistry, Sugar Chemistry Group, University of Gdañsk, 18 Sobieskiego, PL-80-952, Gdañsk, Poland.
Smiataczowa
Kazimiera
K
Kasprzykowska
Regina
R
Dmochowska
Barbara
B
Wiśniewski
Andrzej
A
D001089:Arabinose / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D006851:Hydrochloric Acid / Q000737:chemistry; D007536:Isomerism; D007700:Kinetics; D009005:Monosaccharides / Q000737:chemistry
D003837:Deoxy Sugars; D009005:Monosaccharides; D001089:Arabinose; D006851:Hydrochloric Acid