Unusual Transformations of Mono- and Disaccharide Intermediates in the Synthesis of Oligosaccharides Related to Fragments of the Capsular Polysaccharide of Haemophilus influenzae Type e

Unusual Transformations of Mono- and Disaccharide Intermediates in the Synthesis of Oligosaccharides Related to Fragments of the Capsular Polysaccharide of Haemophilus influenzae Type e Full article

Journal

Doklady Chemistry
ISSN: 1608-3113 , E-ISSN: 0012-5008

Output data

Year: 2023, Volume: 509, Number: 2, Pages: 93-99 Pages count : 7 DOI: 10.1134/s0012500822600390

Authors

Kamneva A.A. ¹ , Yashunsky D.V. ¹ , Gerbst A.G. ¹ , Nifantiev N.E. ¹

Affiliations

1	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia

In the course of synthesis of oligosaccharides related to fragments of the capsular polysaccharide of Haemophilus influenzae type e, reactions of 2-O-trifluoromethanesulfonate β-D-glucopyranoside derivatives with the azide anion were studied. The reactions gave products of both nucleophilic substitution and rearrangement accompanied by 6-membered pyranose ring contraction to a 5-membered ring through (O5–C2)-cyclization. The formation of these products was interpreted for the first time using quantum mechanical calculations.

Kamneva A.A. , Yashunsky D.V. , Gerbst A.G. , Nifantiev N.E.
Unusual Transformations of Mono- and Disaccharide Intermediates in the Synthesis of Oligosaccharides Related to Fragments of the Capsular Polysaccharide of Haemophilus influenzae Type e
Doklady Chemistry. 2023. V.509. N2. P.93-99. DOI: 10.1134/s0012500822600390 WOS Scopus OpenAlex

≡ Web of science:	WOS:001020982300001
≡ Scopus:	2-s2.0-85163875565
≡ OpenAlex:	W4382498974