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 af dette arbejde

Kemisk Institut

22 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Angewandte Chemie - International Edition
Vol/bind	53
Udgave nummer	50
Sider (fra-til)	13889-13893
Antal sider	5
ISSN	1433-7851
DOI	https://doi.org/10.1002/anie.201408209
Status	Udgivet - 2014

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10.1002/anie.201408209

http://www.scopus.com/inward/record.url?scp=84919392302&partnerID=8YFLogxK

Citationsformater

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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",

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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

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