gem-Dimethyl 4-Pentenyl Glycosides: Novel Glycosylating Agents and Anomeric Protecting Groups

gem-Dimethyl 4-Pentenyl Glycosides: Novel Glycosylating Agents and Anomeric Protecting Groups

Two classes of gem-dimethyl 4-n-pentenyl glycosides (i.e., C2-series and C3-series) have been prepared and studied in both the glycosylation and hydrolysis manifolds utilizing NBS as the sole stoichiometric activator. These novel glycosylating agents, which are analogues of Fraser-Reid’s 4-n-penteny...

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Veröffentlicht in:Organic letters 2009-08, Vol.11 (16), p.3594-3597
Hauptverfasser: Fortin, Michael, Kaplan, Justin, Pham, Khoa, Kirk, Sharon, Andrade, Rodrigo B
Format: Artikel
Sprache:eng
Schlagworte:
Glycosides - chemical synthesis
Glycosides - chemistry
Glycosylation
Hydrolysis
Molecular Structure
Stereoisomerism
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Zusammenfassung:Two classes of gem-dimethyl 4-n-pentenyl glycosides (i.e., C2-series and C3-series) have been prepared and studied in both the glycosylation and hydrolysis manifolds utilizing NBS as the sole stoichiometric activator. These novel glycosylating agents, which are analogues of Fraser-Reid’s 4-n-pentenyl glycosyl donors, show increased reactivity in side-by-side studies by virtue of the gem-dimethyl effect.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol901313z