Synthesis of novel dihydrooxazine and oxazoline based sugar hybrids from sugar azides

One-step methods for the synthesis of novel dihydrooxazine and oxazoline-based sugar hybrids are reported. A convenient one-step method for the synthesis of novel dihydrooxazine and oxazoline based sugar hybrids is reported starting from the readily accessible sugar azides and aldehydes. We have use...

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Bibliographic Details
Published in:Tetrahedron letters 2011-08, Vol.52 (33), p.4313-4315
Main Authors: Kurhade, Suresh E., Ravula, Sudhir, Siddaiah, V., Bhuniya, Debnath, Reddy, D. Srinivasa
Format: Article
Language:English
Subjects:
Accessibility
Aldehydes
Backbone
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Dihydrooxazine
Drugs
Exact sciences and technology
Glycoconjugate
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Hydroxy azide
Organic chemistry
Oxazoline
Preparations and properties
Sugar azide
Sugar hybrids
Sugars
Synthesis (chemistry)
Tetrahedrons
Transformations
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Summary:One-step methods for the synthesis of novel dihydrooxazine and oxazoline-based sugar hybrids are reported. A convenient one-step method for the synthesis of novel dihydrooxazine and oxazoline based sugar hybrids is reported starting from the readily accessible sugar azides and aldehydes. We have used Aubé’s protocol to achieve this transformation. The resulting glycoconjugates could be used to increase the diversity on the sugar backbone and may find applications as potential glycomimetics and in drug discovery.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.06.035