UNUSUAL TRANSFORMATIONS OF MONO- AND DISACCHARIDE INTERMEDIATES IN THE SYNTHESIS OF OLIGOSACCHARIDES RELATED TO FRAGMENTS OF THE CAPSULAR POLYSACCHARIDE OF HAEMOPHILUS INFLUENZAE TYPE E

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Abstract

In the course of the synthesis of oligosaccharides related to fragments of the capsular polysaccharide of Haemophilus influenzae type e, the transformations of various 2-O-trifluoromethanesulfonate derivatives of β-D-glucopyranosides in reactions with an azide anion was studied. It gives the products of both nucleophilic substitution and a rearrangement of the 6-membered pyranose ring with its contraction to the 5-membered one through (О-5–С-2)-cyclization. Their formation was interpreted for the first time using quantum mechanical calculations.

About the authors

A. A. Kamneva

N.D. Zelinsky Institute of Organic Chemistry, Laboratory of Glycoconjugate Chemistry, Russian Academy of Sciences

Email: nen@ioc.ac.ru
Russian Federation, 119991, Moscow

D. V. Yashunsky

N.D. Zelinsky Institute of Organic Chemistry, Laboratory of Glycoconjugate Chemistry, Russian Academy of Sciences

Email: nen@ioc.ac.ru
Russian Federation, 119991, Moscow

A. G. Gerbst

N.D. Zelinsky Institute of Organic Chemistry, Laboratory of Glycoconjugate Chemistry, Russian Academy of Sciences

Email: nen@ioc.ac.ru
Russian Federation, 119991, Moscow

N. E. Nifantiev

N.D. Zelinsky Institute of Organic Chemistry, Laboratory of Glycoconjugate Chemistry, Russian Academy of Sciences

Author for correspondence.
Email: nen@ioc.ac.ru
Russian Federation, 119991, Moscow

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Copyright (c) 2023 А.А. Камнева, Д.В. Яшунский, А.Г. Гербст, Н.Э. Нифантьев