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Efficient Two Step β-Glycoside Synthesis from -Acetyl -Glucosamine: Scope and Limitations of Copper(II) Triflate-Catalyzed Glycosylation

Sommer, Roman
; 
Hauck, Dirk
; 
Titz, Alexander
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Abstract
β‐Linked glycosides of N‐acetyl glucosamine are widespread in nature. Their direct synthesis is hampered by the low reactivity of GlcNAc as a glycosyl donor. We report a selective and rapid copper(II) triflate‐catalyzed two‐step synthesis of β‐glycosides of GlcNAc from cheap GlcNAc as starting material without purification of intermediates. α‐Specific glycosylation can be achieved by increasing the amount of catalyst and extending reaction times.
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Affiliation
HIPS, Helmholtz-Institute für pharmazeutische Forschung Saarland, Universitätscampus E8.1, 66123 Saarbrücken, Germany.
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http://hdl.handle.net/10033/621423
DOI
10.1002/slct.201700161
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http://doi.wiley.com/10.1002/slct.201700161
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23656549
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Attribution-NonCommercial-ShareAlike 3.0 United States
cbn
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publications of the junior research group chemical biology of carbohydrates ([HIPS]CBCH)