Acid-catalyzed isomerization of methyl 2-deoxy- d- arabino-hexosides: equilibria, kinetics and mechanism

• Published in: Carbohydrate research Vol. 337; no. 3; pp. 265 - 272
• Main Authors: Nowacki, Andrzej, Smiataczowa, Kazimiera, Kasprzykowska, Regina, Dmochowska, Barbara, Wiśniewski, Andrzej
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier Ltd 11.02.2002
• Subjects: Anomerization; Arabinose - analogs & derivatives; Arabinose - chemistry; Catalysis; Chromatography, High Pressure Liquid - methods; Deoxy Sugars - chemical synthesis; Deoxy Sugars - chemistry; Hydrochloric Acid - chemistry; Isomerism; Isomerization; Kinetic studies; Kinetics; Methyl 2-deoxy- d- arabino-hexosides; Monosaccharides - chemistry; Methyl 2-deoxy- d- arabino-hexosides; Anomerization; Isomerization; Kinetic studies
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(01)00305-6

Four isomers of methyl 2-deoxy- d- arabino-hexosides were isolated by HPLC as chromatographically homogeneous compounds. The rates of pyranoside isomerization (α p and β p ) at 40 °C and of furanoside isomerization (α f and β f ) at 26 °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. Four isomers of methyl 2-deoxy- d- arabino-hexosides were isolated by HPLC as chromatographically homogeneous compounds. The rates of pyranoside isomerization (α p and β p ) at 40 °C and of furanoside isomerization (α f and β f ) at 26 °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.