Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy- and 2,3,6-Trideoxy Sugars.

@article{Nogueira2016ReagentControlledD,
  title={Reagent-Controlled $\alpha$-Selective Dehydrative Glycosylation of 2,6-Dideoxy- and 2,3,6-Trideoxy Sugars.},
  author={Jason M. Nogueira and Marissa Bylsma and Danielle K Bright and Clay S. Bennett},
  journal={Angewandte Chemie},
  year={2016},
  volume={55 34},
  pages={
          10088-92
        },
  url={https://api.semanticscholar.org/CorpusID:29492115}
}
This work has found that activating either 2,3-bis(2,3,4-trimethoxyphenyl)cyclopropenone or 2,1-bis-1-thione with oxalyl bromide results in the formation of a species that promotes the glycosylation between 2,6-dideoxy-sugar hemiacetals and Glycosyl acceptors in good yield and high α-selectivity.
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47 Citations

47 Citations

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The reaction is shown to be effective with a number of glycosyl acceptors, including those possessing acid and base sensitive functionality, and to proceed under mild conditions at room temperature without the need for special dehydrating agents.

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It is shown that 2-deoxy- and 2,6-dideoxyglycosyl bromides can be prepared in high yield and engaged in glycosylation reactions with β:α selectivities ≥6:1 and are compatible with azide-containing donors and acid-sensitive functional groups.

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This paper describes the development of an iterative and α-selective glycosylation method for 2-deoxyglycosyl and 2,6-dideoxythioglycoside donors based on the DMF modulation concept. We used NMR…

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Novel bicyclic glycosyl donors have been prepared by the cycloaddition reaction of glycals with 3-thiono-2,4-pentanedione 17 followed by methylenation of the resulting ketone. Treatment of the…

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A mild and atom-economic gold(I)-catalyzed glycosylation for stereoselective synthesis of 2-deoxy α-glycosides using bench-stable 2-deoxy S-But-3-ynyl thioglycoside donors has been described. Under…

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A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77–97 %) using a trans-fused cyclic 3,4-O-disiloxane…

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