Rapid and efficient synthesis of α(1–2)mannobiosides
File(s)
Author(s)
Reina, José J
Di Maio, Antonio
Ramos-Soriano, Javier
Figueiredo, Rute C
Rojo, Javier
Type
Journal Article
Abstract
α(1,2)mannobiosides with different substituents at the reducing end have been synthesized by a common strategy using benzoyls as the permanent protecting groups and an acetyl as the orthogonal protecting group at position C2 of the glycosyl acceptor. The new synthetic strategy has been performed remarkably reducing the number of purification steps, the time of synthesis (less than 72 hours) and improving the overall yield at least three times with respect to the best procedure described in the literature at the moment. Additionally, this protecting group strategy is compatible with the presence of azido groups and the use of Cu catalyzed azide alkyne cycloaddition (CuAAC) also called “click chemistry” for conjugating the α(1–2)mannobiosides to different scaffolds for the preparation of mannosyl multivalent systems.
Date Acceptance
2016-02-02
Citation
Organic and Biomolecular Chemistry, 14 (10), pp.2873-2882
ISSN
1477-0520
Publisher
Royal Society of Chemistry
Start Page
2873
End Page
2882
Journal / Book Title
Organic and Biomolecular Chemistry
Volume
14
Issue
10
Copyright Statement
© The Royal Society of Chemistry 2016. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
License URL
Identifier
https://pubs.rsc.org/en/content/articlelanding/2016/OB/C6OB00083E
Publication Status
Published
Date Publish Online
2016-02-02