Highly Selective Formation of β-Glycosides of N-Acetylglucosamine Using Catalytic Iron(III) Triflate

Efficient and highly selective glycosylation reactions of peracetylated β‐D‐N‐acetylglucosamine are described using catalytic iron(III) triflate and 2,4,6‐tri‐tert‐butylpyrimidine (TTBP) under microwave conditions. We have demonstrated that the formation of β‐(1→6) and β‐(1→3) linked disaccharides a...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2012-03, Vol.2012 (9), p.1699-1702
Main Authors: Stévenin, Arnaud, Boyer, François-Didier, Beau, Jean-Marie
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemical Sciences
Chemistry
Exact sciences and technology
Glycosides
Glycosylation
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Iron
Lewis acids
Organic chemistry
Preparations and properties
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Summary:Efficient and highly selective glycosylation reactions of peracetylated β‐D‐N‐acetylglucosamine are described using catalytic iron(III) triflate and 2,4,6‐tri‐tert‐butylpyrimidine (TTBP) under microwave conditions. We have demonstrated that the formation of β‐(1→6) and β‐(1→3) linked disaccharides are obtained in high yields in the presence ofvarious protecting groups. The inexpensive and environmentallyfriendly promoter system composed of catalytic amounts of stable and nonhygroscopic iron(III) triflate·solvate and 2,4,6‐tri‐tert‐butylpyrimidine (TTBP) activates efficiently the commercially available β‐pentaacetate of N‐acetylglucosamine in the direct synthesis of the important β‐GlcNAc motif.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201200062