Stabilization of sialyl cation in axial conformation assisted by remote acyl groups

Stabilization of sialyl cation in axial conformation assisted by remote acyl groups Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2018, Volume: 67, Number: 9, Pages: 1573-1579 Pages count : 7 DOI: 10.1007/s11172-018-2260-y

Authors

Panova M.V. ¹ , Orlova A.V. ¹ , Kononov L.O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

Stereoselective synthesis of α-sialosides by the glycosylation reaction (sialylation) is an important task in carbohydrate chemistry. Using quantum chemical calculations, the conformations of the sialyl cation formed from the sialyl donor under conditions of sialylation reaction were studied. Although the "axial conformation" of sialyl cation itself is energetically unfavorable, it is possible to stabilize it through the participation of O- and N-acyl protective groups. The obtained results open the possibility to modulate the stereoselectivity of sialylation by directed variation of the nature of protective groups in the sialyl donor molecule. 2

Panova M.V. , Orlova A.V. , Kononov L.O.
Stabilization of sialyl cation in axial conformation assisted by remote acyl groups
Russian Chemical Bulletin. 2018. V.67. N9. P.1573-1579. DOI: 10.1007/s11172-018-2260-y WOS Scopus OpenAlex

Web of science:	WOS:000449756500004
Scopus:	2-s2.0-85056272141
OpenAlex:	W2900350036

DB	Citing
OpenAlex	7
Scopus	6
Web of science	6