From methyl
-glucopyranoside to methyl
-allopyranoside via the Mitsunobu reaction |
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Authors: | Mikhail Kim Barbara Grzeszczyk Aleksander Zamojski |
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Abstract: | Methyl β-
-glucopyranoside reacted with a 4-molar excess of the Mitsunobu reagents (triphenylphosphine–diethyl azodicarboxylate–benzoic acid) under Weinges et al. Carbohydr. Res., 164 (1987) 453–458] conditions to furnish four differently benzoylated methyl β-
-allopyranosides in a very good overall yield. The same reaction applied to methyl α-
-glucopyranoside yielded allosides in a low yield and nine other sugar products. These results give an insight into the course of the Mitsunobu esterification–inversion reaction. |
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Keywords: | Methyl α - and β -
-glucopyranosides Benzoylated methyl α - and β -
-allopyranosides Mitsunobu reaction |
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