A convenient synthesis of novel pyrano[2,3-b][1,5]oxazepines via ring closure of O-glycosyl amino acids

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2011
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Khodair, Ahmed
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European Journal of Organic Chemistry. 2011, 2011(36), pp. 7407-7413. ISSN 1434-193X. Available under: doi: 10.1002/ejoc.201101148
Zusammenfassung

N-Boc-protected serine and threonine esters could be readily added to 2-nitroglycals, affording exclusively α- and β-anomers with galacto- and gluco-configuration, respectively. Nitro group reduction to the amino group and also ester cleavage led to compounds 2, 6, and 11, which can be regarded as dipeptide mimetics. From these compounds, bicyclic pyrano[2.3-b][1,5]oxazepines 7–14 were prepared by ring closure.

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540 Chemie
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Cyclization, Diastereoselectivity, Enantioselectivity, Glycoconjugates, Glycosides, Michael addition
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ISO 690KHODAIR, Ahmed, Richard R. SCHMIDT, 2011. A convenient synthesis of novel pyrano[2,3-b][1,5]oxazepines via ring closure of O-glycosyl amino acids. In: European Journal of Organic Chemistry. 2011, 2011(36), pp. 7407-7413. ISSN 1434-193X. Available under: doi: 10.1002/ejoc.201101148
BibTex
@article{Khodair2011conve-18130,
  year={2011},
  doi={10.1002/ejoc.201101148},
  title={A convenient synthesis of novel pyrano[2,3-b][1,5]oxazepines via ring closure of O-glycosyl amino acids},
  number={36},
  volume={2011},
  issn={1434-193X},
  journal={European Journal of Organic Chemistry},
  pages={7407--7413},
  author={Khodair, Ahmed and Schmidt, Richard R.}
}
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