Abstract: A series of novel sialyl donors containing O-trifluoroacetyl (TFA) groups at various positions was synthesized. The choice of protecting groups in sialyl donors was based on hypothesis that variations in ability of different acyl groups to act as hydrogen bond acceptors would influence the supramolecular structure of reaction mixture (solution structure), hence the outcome of sialylation. These glycosyl donors were examined in the model glycosylation of the primary hydroxyl group of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose in comparison with sialyl donors without O-TFA groups. The presence of O-TFA groups in a sialyl donor strongly affected the outcome of sialylation. Several sialyl donors studied showed promising results: yields of disaccharides can be as high as 86% as can be the stereoselectivities (α/β up to 15:1). The results obtained suggest that varying acyl O-protecting groups in sialyl donor may result in dramatic changes in the outcome of sialylation although further studies are required to dissect the influence of intermolecular hydrogen bonding and intramolecular substituent effects related to variations of electron-withdrawing properties of different acyl groups.

Cite: Podvalnyy N.M. , Malysheva N.N. , Panova M.V. , Zinin A.I. , Chizhov A.O. , Orlova A.V. , Kononov L.O.
Stereoselective sialylation with O-trifluoroacetylated thiosialosides: hydrogen bonding involved?
Carbohydrate Research. 2017. V.451. P.12-28. DOI: 10.1016/j.carres.2017.09.002 WOS Scopus OpenAlex

Identifiers:

Web of science:	WOS:000413320300002
Scopus:	2-s2.0-85029484230
OpenAlex:	W2753165348

Citing:

DB	Citing
OpenAlex	21
Scopus	22
Web of science	21

Altmetrics: