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  • Title: Acid-catalyzed isomerization of methyl 2-deoxy-D-arabino-hexosides: equilibria, kinetics and mechanism.
    Author: Nowacki A, Smiataczowa K, Kasprzykowska R, Dmochowska B, Wiśniewski A.
    Journal: Carbohydr Res; 2002 Feb 11; 337(3):265-72. PubMed ID: 11844496.
    Abstract:
    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.
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