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

A. A. Kamneva; Камнева А. А.; D. V. Yashunsky; Яшунский Д. В.; A. G. Gerbst; Гербст А. Г.; N. E. Nifantiev; Нифантьев Н. Э.

doi:10.31857/S2686953523600162

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

Authors: Kamneva A.A.¹, Yashunsky D.V.¹, Gerbst A.G.¹, Nifantiev N.E.¹
Affiliations:
1. N.D. Zelinsky Institute of Organic Chemistry, Laboratory of Glycoconjugate Chemistry, Russian Academy of Sciences
Issue: Vol 509, No 1 (2023)
Pages: 22-29
Section: CHEMISTRY
URL: https://journal-vniispk.ru/2686-9535/article/view/135955
DOI: https://doi.org/10.31857/S2686953523600162
EDN: https://elibrary.ru/OWAYCI
ID: 135955

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Abstract
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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.

Keywords

density functional method, nucleophilic substitution, cycle narrowing, transition states

References

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