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Organocatalysis for the Acid-Free O-Arylidenation of Carbohydrates

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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:352-260640
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https://doi.org/10.1002/ejoc.201301116
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European Journal of Organic Chemistry. 2013, 2013(31), pp. 7035-7040. ISSN 1434-193X. eISSN 0365-5490. Available under: doi: 10.1002/ejoc.201301116

Zusammenfassung

Methyl glycopyranosides of glucose, galactose, and mannose, their 2,3-di-O-benzyl-protected derivatives, as well as the unprotected sugars react with p-methoxybenzaldehyde dimethyl acetal (3) and with benzaldehyde dimethyl acetal (7) as reagents in the presence of thiourea 1 or squaramide 2 as the organocatalyst to afford regioselectively 4,6-O-arylidenated derivatives 5 and 8. With an excess amount of 3 or 7, diarylidenated derivatives are also obtained. In situ formation of acetals of type 3 and 7 from corresponding aldehydes 10 and 13 in the presence of an orthoester and organocatalyst 1 or 2 can be used to generate 5 and 8 directly from the aldehydes. Some substrates also lead to mixed orthoesters with this procedure. The reaction courses are discussed.

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Fachgebiet (DDC)
540 Chemie

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Acetals, Carbohydrates, Organocatalysis, Protecting groups, Synthetic methods

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ISO 690GENG, Yiqun, Amit KUMAR, Hassan M. FAIDALLAH, Hassan A. ALBAR, Ibrahim A. MHKALID, Richard R. SCHMIDT, 2013. Organocatalysis for the Acid-Free O-Arylidenation of Carbohydrates. In: European Journal of Organic Chemistry. 2013, 2013(31), pp. 7035-7040. ISSN 1434-193X. eISSN 0365-5490. Available under: doi: 10.1002/ejoc.201301116
BibTex
@article{Geng2013Organ-26064,
  year={2013},
  doi={10.1002/ejoc.201301116},
  title={Organocatalysis for the Acid-Free O-Arylidenation of Carbohydrates},
  number={31},
  volume={2013},
  issn={1434-193X},
  journal={European Journal of Organic Chemistry},
  pages={7035--7040},
  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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