… Substituent Effect on the Anomerization of Pyranosides: Mechanism of Anomerization and Synthesis of a 1, 2??cis Glucosamine Oligomer from the 1, 2??trans Anomer

S Manabe, H Satoh, J Hutter, HP Lüthi…

Index: Manabe, Shino; Satoh, Hiroko; Hutter, Juerg; Luethi, Hans Peter; Laino, Teodoro; Ito, Yukishige Chemistry - A European Journal, 2014 , vol. 20, # 1 p. 124 - 132

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Citation Number: 8

Abstract

Abstract Aminoglycosides containing a 2, 3-trans carbamate group easily undergo anomerization from the 1, 2-trans glycoside to the 1, 2-cis isomer under mild acidic conditions. The N-substituent of the carbamate has a significant effect on the anomerization reaction; in particular, an N-acetyl group facilitated rapid and complete α-anomerization. The differences in reactivity due to the various N-substituents were supported by the results of ...