Реферат: Great interest in natural furanoside-containing compounds has challenged the development of preparative methods for their synthesis. Herein a novel reaction in carbohydrate chemistry, namely a pyranoside-into-furanoside (PIF) rearrangement permitting the transformation of selectively O-substituted pyranosides into the corresponding furanosides is reported. The discovered process includes acid-promoted sulfation accompanied by rearrangement of the pyranoside ring into a furanoside ring followed by solvolytic O-desulfation. This process, which has no analogy in organic chemistry, was shown to be a very useful tool for the synthesis of furanoside-containing complex oligosaccharides, which was demonstrated by synthesizing disaccharide derivatives α-D-Galp-(1→3)-β-D-Galf-OPr, 3-O-s-lactyl-β-D-Galf-(1→3)-β-D-Glcp-OPr, and α-L-Fucf-(1→4)-β-D-GlcpA-OPr related to polysaccharides from the bacteria Klebsiella pneumoniae and Enterococcus faecalis and the brown seaweed Chordaria flagelliformis.

Библиографическая ссылка: Krylov V.B. , Argunov D.A. , Vinnitskiy D.Z. , Verkhnyatskaya S.A. , Gerbst A.G. , Ustyuzhanina N.E. , Dmitrenok A.S. , Huebner J. , Holst O. , Siebert H-C. , Nifantiev N.E.
Pyranoside‐into‐Furanoside Rearrangement: New Reaction in Carbohydrate Chemistry and Its Application in Oligosaccharide Synthesis
Chemistry: A European Journal. 2014. V.20. N50. P.16516-16522. DOI: 10.1002/chem.201405083 WOS Scopus OpenAlex

Идентификаторы БД:

≡ Web of science:	WOS:000346055800016
≡ Scopus:	2-s2.0-84924671798
≡ OpenAlex:	W2138644438

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