β-Selective xylulofuranosylation via a conformationally-restricted glycosyl donor

Literature Information

Publication Date 2020-02-28
DOI 10.1039/D0OB00260G
Impact Factor 3.876
Authors

Bo-Shun Huang, Todd L. Lowary


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Abstract

Reported is the first stereoselective method for β-xylulofuranosylation, which employs 3,4-O-xylylene-protected thioglycoside donors. For most acceptors, the best results were observed with a donor (8) that possesses both the xylylene group and a benzoate ester at O-1. To demonstrate its utility, the methodology was applied to the first synthesis of the pentasaccharide repeating unit from the lipopolysaccharide O-antigen of Yersinia enterocolitica serovars O:5/O:5,27, a structure containing two β-xylulofuranose residues.

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Back cover

2023-11-20 Cover

DOI: 10.1039/D3NH90058D

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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