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 (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 transform...

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Published inCarbohydrate research Vol. 337; no. 3; pp. 265 - 272
Main Authors Nowacki, Andrzej, Smiataczowa, Kazimiera, Kasprzykowska, Regina, Dmochowska, Barbara, Wiśniewski, Andrzej
Format Journal Article
LanguageEnglish
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
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Abstract 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.
AbstractList 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.
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.
Author Kasprzykowska, Regina
Wiśniewski, Andrzej
Smiataczowa, Kazimiera
Dmochowska, Barbara
Nowacki, Andrzej
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Cites_doi 10.1002/cber.19220550122
10.1139/v62-038
10.1002/cber.19230560511
10.1039/JR9490002846
10.1016/S0008-6215(00)84949-6
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10.1080/07328309908543976
10.1039/JR9550004419
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Keywords Methyl 2-deoxy- d- arabino-hexosides
Anomerization
Isomerization
Kinetic studies
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Snippet Four isomers of methyl 2-deoxy- d- arabino-hexosides were isolated by HPLC as chromatographically homogeneous compounds. The rates of pyranoside isomerization...
Four isomers of methyl 2-deoxy-D-arabino-hexosides were isolated by HPLC as chromatographically homogeneous compounds. The rates of pyranoside isomerization...
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StartPage 265
SubjectTerms 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
Title Acid-catalyzed isomerization of methyl 2-deoxy- d- arabino-hexosides: equilibria, kinetics and mechanism
URI https://dx.doi.org/10.1016/S0008-6215(01)00305-6
https://www.ncbi.nlm.nih.gov/pubmed/11844496
https://search.proquest.com/docview/71446873
Volume 337
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