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Cooperative Catalysis in Glycosidation Reactions with O-Glycosyl Trichloroacetimidates as Glycosyl Donors

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2013

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Faidallah, Hassan M.
Albar, Hassan A.
Mhkalid, Ibrahim A.

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http://nbn-resolving.de/urn:nbn:de:bsz:352-260635
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https://doi.org/10.1002/anie.201302158
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Angewandte Chemie International Edition. 2013, 52(38), pp. 10089-10092. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201302158

Zusammenfassung

Thiourea mediates cooperative glycosidation through hydrogen bonding. N,N′-Diarylthiourea as cocatalyst enforces an SN2-type acid-catalyzed glycosidation even at room temperature (see scheme; Bn=benzyl). From O-(α-glycosyl) trichloroacetimidates as glycosyl donors and various acceptors, β-glycosides are preferentially or exclusively obtained.

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ISO 690GENG, Yiqun, Amit KUMAR, Hassan M. FAIDALLAH, Hassan A. ALBAR, Ibrahim A. MHKALID, Richard R. SCHMIDT, 2013. Cooperative Catalysis in Glycosidation Reactions with O-Glycosyl Trichloroacetimidates as Glycosyl Donors. In: Angewandte Chemie International Edition. 2013, 52(38), pp. 10089-10092. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201302158
BibTex
@article{Geng2013-09-16Coope-26063,
  year={2013},
  doi={10.1002/anie.201302158},
  title={Cooperative Catalysis in Glycosidation Reactions with O-Glycosyl Trichloroacetimidates as Glycosyl Donors},
  number={38},
  volume={52},
  issn={1433-7851},
  journal={Angewandte Chemie International Edition},
  pages={10089--10092},
  author={Geng, Yiqun and Kumar, Amit and Faidallah, Hassan M. and Albar, Hassan A. and Mhkalid, Ibrahim A. and Schmidt, Richard R.}
}
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