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Reversal of Anomeric Selectivity with O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis

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2012

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http://nbn-resolving.de/urn:nbn:de:bsz:352-216329
DOI (zitierfähiger Link)
https://doi.org/10.1002/ejoc.201200138
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European Journal of Organic Chemistry. 2012, 2012(14), pp. 2715-2719. ISSN 1434-193X. eISSN 1099-0690. Available under: doi: 10.1002/ejoc.201200138

Zusammenfassung

Boron trifluoride or trimethylsilyl trifluoromethanesulfonate catalysed the generation of thioglycosides from O-glucopyranosyl or O-galactopyranosyl trichloroacetimidates and thiols giving mainly or exclusively α-thioglycosides. However, the same reactions with phenylboron difluoride as catalyst are highly β-selective. An SN2-type reaction course under acid/base catalysis is invoked by these and previous results.

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Fachgebiet (DDC)
540 Chemie

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Carbohydrates, Glycosylation, Thioglycosylation, Reaction mechanisms

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ISO 690KUMAR, Amit, Richard R. SCHMIDT, 2012. Reversal of Anomeric Selectivity with O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis. In: European Journal of Organic Chemistry. 2012, 2012(14), pp. 2715-2719. ISSN 1434-193X. eISSN 1099-0690. Available under: doi: 10.1002/ejoc.201200138
BibTex
@article{Kumar2012Rever-21632,
  year={2012},
  doi={10.1002/ejoc.201200138},
  title={Reversal of Anomeric Selectivity with O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis},
  number={14},
  volume={2012},
  issn={1434-193X},
  journal={European Journal of Organic Chemistry},
  pages={2715--2719},
  author={Kumar, Amit and Schmidt, Richard R.}
}
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