Intramolecular Glycosidation by Click Reaction Mediated Spacer Generation and Following Spacer Cleavage

Kumar, Amit; Geng, Yiqun; Schmidt, Richard R.

Intramolecular Glycosidation by Click Reaction Mediated Spacer Generation and Following Spacer Cleavage

Dateien

kumar_216336.pdfGröße: 389.82 KBDownloads: 264

Datum

2012

Open Access-Veröffentlichung

Open Access Green

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

European Journal of Organic Chemistry. 2012, 2012(35), pp. 6846-6851. ISSN 1434-193X. eISSN 1099-0690. Available under: doi: 10.1002/ejoc.201201076

Zusammenfassung

2-O-Propargyl-substituted glycosyl donors and O-(2-azidobenzyl)-substituted acceptors having a vicinal hydroxy group readily underwent the click reaction. Intramolecular glycosidation with N-iodosuccinimide/trifluoromethansulfonic acid as the activating system afforded β-(1–3)- and α-(1–2)-linked disaccharides as part of 14-membered macrocycles. Descriptors for these reactions are proposed that consider the donor and acceptor attachment sites and the stereochemistry of the functional groups. Investigation of the influence of 2-O-linked 1-aryl-1,2,3-triazol-4-ylmethyl groups, as contained in the spacer, on the anomeric selectivity exhibited no anchimeric assistance. In addition, it was shown that the spacer group can be readily cleaved under Birch reduction conditions.

Fachgebiet (DDC)

540 Chemie

Schlagwörter

Glycosides, Stereoselectivity, Click chemistry, Macrocycles

Zitieren

ISO 690

KUMAR, Amit, Yiqun GENG, Richard R. SCHMIDT, 2012. Intramolecular Glycosidation by Click Reaction Mediated Spacer Generation and Following Spacer Cleavage. In: European Journal of Organic Chemistry. 2012, 2012(35), pp. 6846-6851. ISSN 1434-193X. eISSN 1099-0690. Available under: doi: 10.1002/ejoc.201201076

BibTex

@article{Kumar2012Intra-21633,
  year={2012},
  doi={10.1002/ejoc.201201076},
  title={Intramolecular Glycosidation by Click Reaction Mediated Spacer Generation and Following Spacer Cleavage},
  number={35},
  volume={2012},
  issn={1434-193X},
  journal={European Journal of Organic Chemistry},
  pages={6846--6851},
  author={Kumar, Amit and Geng, Yiqun and Schmidt, Richard R.}
}

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