Hydrogen-Bond-Mediated Aglycone Delivery: Focus on β‑Mannosylation

Hydrogen-Bond-Mediated Aglycone Delivery: Focus on β‑Mannosylation

O-Picoloyl groups at remote positions can mediate the course of glycosylation reactions by providing high facial selectivity for the H-bond-mediated attack of the glycosyl acceptor. A new practical method for the stereoselective synthesis of β-mannosides at ambient temperature is presented.

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Veröffentlicht in:Organic letters 2014-02, Vol.16 (3), p.716-719
Hauptverfasser: Pistorio, Salvatore G, Yasomanee, Jagodige P, Demchenko, Alexei V
Format: Artikel
Sprache:eng
Schlagworte:
Glycosylation
Hydrogen - chemistry
Hydrogen Bonding
Mannosides - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:O-Picoloyl groups at remote positions can mediate the course of glycosylation reactions by providing high facial selectivity for the H-bond-mediated attack of the glycosyl acceptor. A new practical method for the stereoselective synthesis of β-mannosides at ambient temperature is presented.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403396j