A comparative study of the influence of some protecting groups on the reactivity of D-glucosamine acceptors with a galactofuranosyl donor

Carbohydrate Research
María L BohnEdmundo A Rúveda

Abstract

Competitive glycosylation experiments with a galactofuranosyl trichloroacetimidate donor were performed with glucosamine acceptors having a free 4-OH group and carrying different protecting groups at N-2, O-3, and O-6. The most reactive acceptor is the N-dimethylmaleimido 3,6-di-O-benzylated derivative (6c), which reacts even faster than the oxazolidinone 1a. Molecular orbital calculations have helped to rationalize these experimental facts in terms of a hard-hard reaction occurring between the donor and the acceptor.

References

Sep 1, 1995·Glycobiology·R M de Lederkremer, W Colli

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Citations

Jan 29, 2009·Angewandte Chemie·Xiangming Zhu, Richard R Schmidt
Jun 18, 2009·Chemistry : a European Journal·Shino ManabeYukishige Ito
Jul 10, 2019·Chemical Society Reviews·Stefan van der VormJeroen D C Codée
May 30, 2017·Chemical Science·S van der VormJ D C Codée
Apr 29, 2008·Carbohydrate Research·Pauline PeltierVincent Ferrières
Jan 2, 2010·Carbohydrate Research·Verónica M MendozaCarola Gallo-Rodriguez

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