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

Tobias Frihed; Christian Marcus Pedersen; Mikael Bols

doi:10.1002/anie.201408209

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

Tobias Frihed, Christian Marcus Pedersen^*, Mikael Bols

^*Corresponding author for this work

Department of Chemistry

22 Citations (Scopus)

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.

Original language	English
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	50
Pages (from-to)	13889-13893
Number of pages	5
ISSN	1433-7851
DOIs	https://doi.org/10.1002/anie.201408209
Publication status	Published - 2014

Keywords

C-H activation
Fleming-Tamao oxidation
Glycosyl donors
Iridium catalysis
L-hexoses

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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",

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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

SN - 1433-7851

VL - 53

SP - 13889

EP - 13893

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 50

ER -

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

Abstract

Keywords

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