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Heuckendorff M, Bendix J, Pedersen CM, et al. β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor. Org Lett. 2014;16(4):1116-9doi: 10.1021/ol403722f.
Heuckendorff, M., Bendix, J., Pedersen, C. M., & Bols, M. (2014). β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor. Organic letters, 16(4), 1116-9. https://doi.org/10.1021/ol403722f
Heuckendorff, Mads, et al. "β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor." Organic letters vol. 16,4 (2014): 1116-9. doi: https://doi.org/10.1021/ol403722f
Heuckendorff M, Bendix J, Pedersen CM, Bols M. β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor. Org Lett. 2014 Feb 21;16(4):1116-9. doi: 10.1021/ol403722f. Epub 2014 Feb 06. PMID: 24502365.
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Org Lett. 2014 Feb 21;16(4):1116-9. doi: 10.1021/ol403722f. Epub 2014 Feb 06.

β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor.

Organic letters

Mads Heuckendorff, Jesper Bendix, Christian M Pedersen, Mikael Bols

Affiliations

  1. Department of Chemistry, University of Copenhagen , Universitetsparken 5, 2100 Copenhagen Ø, Denmark.

PMID: 24502365 DOI: 10.1021/ol403722f

Abstract

Mannosylations using the new conformationally restricted donor phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-α-D-mannopyranoside (6) have been found to be β-selective with a variety of activation conditions. The simplest activation conditions were NIS/TfOH, in which case it is proposed that the β-mannoside is formed from β-selective glycosylation of the oxocarbenium ion 25 in a B(2,5) conformation.

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