Universität zu Köln

Korber, Nora Katharina and Pedersen, Christian Marcus (2022). Slow glycosylation: Activation of trichloroacetimidates under mild conditions using lithium salts and the role of counterions. Carbohydr. Res., 511. OXFORD: ELSEVIER SCI LTD. ISSN 1873-426X

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Abstract

Glycosylations were carried out with the two glycosyl donors 4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-alpha-L-rhamnopyranose and 2,3,4-tri-O-benzyl-1-O-trichloro-acetimidoyl-alpha-L-rhamnopyranose in combination with the two alcohols 1-adamantanol and L-menthol as model glycosyl acceptors. As catalysts, the five lithium salts LiNTf2, LiI, LiClO4, LiPF6 and LiOTf were investigated. We demonstrated that both lithium and the respective counterions are playing a role in the activation of trichloroacetimidate glycosyl donors at rt. Under these very mild conditions, the glycosylations are slow and completed in two to eight days. Depending on the counterion, the rate and yield of the reaction differs; however, the selectivity of all investigated lithium salts is deficient.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Korber, Nora Katharina UNSPECIFIED UNSPECIFIED UNSPECIFIED Pedersen, Christian Marcus UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-664310
DOI:	10.1016/j.carres.2021.108497
Journal or Publication Title:	Carbohydr. Res.
Volume:	511
Date:	2022
Publisher:	ELSEVIER SCI LTD
Place of Publication:	OXFORD
ISSN:	1873-426X
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language FACILE SYNTHESIS; GLYCOSIDES; CLEISTETROSIDE-2; RHAMNOSYLATION; CONFIGURATION Multiple languages Biochemistry & Molecular Biology; Chemistry, Applied; Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/66431