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
Full text not available from this repository.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: |
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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 | ||||||||||||
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URI: | http://kups.ub.uni-koeln.de/id/eprint/66431 |
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