Highly Facialselective Synthesis of Pyranose 1,3-Oxazines and Their Ring Opening with Nucleophiles: A Novel Entry to 2-C-Branched Glycosides

Highly Facialselective Synthesis of Pyranose 1,3-Oxazines and Their Ring Opening with Nucleophiles: A Novel Entry to 2-C-Branched Glycosides

A TMSOTf-promoted cycloaddition of N-benzoyl-N,O-acetals with various glycals and 3-deoxy glycals affords pyranose 1,3-oxazines with high facial selectivity. In addition, a highly diastereoselective ring opening of the resulting pyranose 1,3-oxazines is reported. With diverse nucleophiles, these rea...

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Veröffentlicht in:Organic letters 2011-10, Vol.13 (19), p.5088-5091
Hauptverfasser: Yin, Biao-Lin, Zhang, Ze-Ren, Xu, Li-Wen, Jiang, Huanfeng
Format: Artikel
Sprache:eng
Schlagworte:
Carbon - chemistry
Glycosides - chemistry
Molecular Structure
Oxazines - chemical synthesis
Stereoisomerism
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Zusammenfassung:A TMSOTf-promoted cycloaddition of N-benzoyl-N,O-acetals with various glycals and 3-deoxy glycals affords pyranose 1,3-oxazines with high facial selectivity. In addition, a highly diastereoselective ring opening of the resulting pyranose 1,3-oxazines is reported. With diverse nucleophiles, these reactions take place upon heating at 80 °C. This novel ring-opening reaction affords structurally diversified 2-C-branched glycosides with three newly formed contiguous stereocenters.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2019604