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Silicon Fluorides for Acid-Base Catalysis in Glycosidations

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2012

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http://nbn-resolving.de/urn:nbn:de:bsz:352-216299
DOI (zitierfähiger Link)
https://doi.org/10.1002/adsc.201100933
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Chemie: Publikationen
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Advanced Synthesis & Catalysis. 2012, 354(8), pp. 1489-1499. ISSN 1615-4150. eISSN 1615-4169. Available under: doi: 10.1002/adsc.201100933

Zusammenfassung

Adduct formation between alcohols as glycosyl acceptors and phenylsilicon trifluoride (PhSiF3)as catalyst permits acid-base-atalyzed glycosidations with O-glycosyl trichloroacetimidates as glycosyl donors. In this way, from various glycosyl donors and acceptors 1,2-trans- and some 1,2-cis-glycosides could be obtained with high anomeric selectivity. A preference for an intramolecular bimolecular nucleophilic substitution (SN2-type) reaction course with concomitant donor and acceptor activation is supported by the results.

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Fachgebiet (DDC)
540 Chemie

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arylsilicon fluorides, bifunctional catalysis, glycosidation, 1, 2-trans glycosides, O-glycosyl trichloroacetimidates, mechanism

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ISO 690KUMAR, Amit, Yiqun GENG, Richard R. SCHMIDT, 2012. Silicon Fluorides for Acid-Base Catalysis in Glycosidations. In: Advanced Synthesis & Catalysis. 2012, 354(8), pp. 1489-1499. ISSN 1615-4150. eISSN 1615-4169. Available under: doi: 10.1002/adsc.201100933
BibTex
@article{Kumar2012Silic-21629,
  year={2012},
  doi={10.1002/adsc.201100933},
  title={Silicon Fluorides for Acid-Base Catalysis in Glycosidations},
  number={8},
  volume={354},
  issn={1615-4150},
  journal={Advanced Synthesis & Catalysis},
  pages={1489--1499},
  author={Kumar, Amit and Geng, Yiqun and Schmidt, Richard R.}
}
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