Synthesis of all eight L-glycopyranosyl donors using C-H activation

Research output: Contribution to journal › Journal article › Research › peer-review

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Synthesis of all eight L-glycopyranosyl donors using C-H activation. / Frihed, Tobias; Pedersen, Christian Marcus; Bols, Mikael.

In: Angewandte Chemie - International Edition, Vol. 53, No. 50, 2014, p. 13889-13893.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Frihed, T, Pedersen, CM & Bols, M 2014, 'Synthesis of all eight L-glycopyranosyl donors using C-H activation', Angewandte Chemie - International Edition, vol. 53, no. 50, pp. 13889-13893. https://doi.org/10.1002/anie.201408209

APA

Frihed, T., Pedersen, C. M., & Bols, M. (2014). Synthesis of all eight L-glycopyranosyl donors using C-H activation. Angewandte Chemie - International Edition, 53(50), 13889-13893. https://doi.org/10.1002/anie.201408209

Vancouver

Frihed T, Pedersen CM, Bols M. Synthesis of all eight L-glycopyranosyl donors using C-H activation. Angewandte Chemie - International Edition. 2014;53(50):13889-13893. https://doi.org/10.1002/anie.201408209

Author

Frihed, Tobias ; Pedersen, Christian Marcus ; Bols, Mikael. / Synthesis of all eight L-glycopyranosyl donors using C-H activation. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 50. pp. 13889-13893.

Bibtex

@article{c0423df94c4c4cfa8a7ab5f17d9b6fba,
title = "Synthesis of all eight L-glycopyranosyl donors using C-H activation",
abstract = "The synthesis of all eight rare, but biologically important L-hexoses as the according thioglycosyl donors was achieved through a procedure involving the C-H activation of their corresponding 6-deoxy-L-hexoses. The key steps of the procedure were the silylation of the OH group at C4 followed by an intramolecular C-H activation of the methyl group in g-position; both steps were catalyzed by iridium. The following Fleming-Tamao oxidation and acetylation gave the suitably protected L-hexoses. This is the first general method for the preparation of all eight L-hexoses as their thioglycosyl donors ready for glycosylation and the first example of an iridium-catalyzed C(sp3)-H activation on sulfide-containing compounds.",
keywords = "C-H activation, Fleming-Tamao oxidation, Glycosyl donors, Iridium catalysis, L-hexoses",
author = "Tobias Frihed and Pedersen, {Christian Marcus} and Mikael Bols",
year = "2014",
doi = "10.1002/anie.201408209",
language = "English",
volume = "53",
pages = "13889--13893",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
publisher = "Wiley-VCH Verlag GmbH & Co. KGaA",
number = "50",

}

RIS

TY - JOUR

T1 - Synthesis of all eight L-glycopyranosyl donors using C-H activation

AU - Frihed, Tobias

AU - Pedersen, Christian Marcus

AU - Bols, Mikael

PY - 2014

Y1 - 2014

N2 - The synthesis of all eight rare, but biologically important L-hexoses as the according thioglycosyl donors was achieved through a procedure involving the C-H activation of their corresponding 6-deoxy-L-hexoses. The key steps of the procedure were the silylation of the OH group at C4 followed by an intramolecular C-H activation of the methyl group in g-position; both steps were catalyzed by iridium. The following Fleming-Tamao oxidation and acetylation gave the suitably protected L-hexoses. This is the first general method for the preparation of all eight L-hexoses as their thioglycosyl donors ready for glycosylation and the first example of an iridium-catalyzed C(sp3)-H activation on sulfide-containing compounds.

AB - The synthesis of all eight rare, but biologically important L-hexoses as the according thioglycosyl donors was achieved through a procedure involving the C-H activation of their corresponding 6-deoxy-L-hexoses. The key steps of the procedure were the silylation of the OH group at C4 followed by an intramolecular C-H activation of the methyl group in g-position; both steps were catalyzed by iridium. The following Fleming-Tamao oxidation and acetylation gave the suitably protected L-hexoses. This is the first general method for the preparation of all eight L-hexoses as their thioglycosyl donors ready for glycosylation and the first example of an iridium-catalyzed C(sp3)-H activation on sulfide-containing compounds.

KW - C-H activation

KW - Fleming-Tamao oxidation

KW - Glycosyl donors

KW - Iridium catalysis

KW - L-hexoses

U2 - 10.1002/anie.201408209

DO - 10.1002/anie.201408209

M3 - Journal article

C2 - 25303081

AN - SCOPUS:84919392302

VL - 53

SP - 13889

EP - 13893

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 50

ER -

ID: 131020865