Rapid and efficient synthesis of α(1–2)mannobiosides. Issue 10 (11th February 2016)

• Record Type: Journal Article
• Authors: Reina, José J.; Di Maio, Antonio; Ramos-Soriano, Javier; Figueiredo, Rute C.; Rojo, Javier
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 10(2016)
• Page Start: 2873
• Page End: 2882
• Publication Date: 2016-02-11
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00083e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A very rapid, versatile and high yield synthesis of Manα1, 2Man derivatives using a common orthogonal benzoyl/acetyl protection strategy compatible with the presence of azido groups and the use of CuAAC for conjugating the α(1–2)mannobiosides to different scaffolds, reducing the cost and time of the synthesis and improving the overall yield. 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.