Work

Structural Bias Effect On Azidation at C-1 and C-2 of Alkyl-3,6-anhydro- d -hexofuranosides: Synthetic Approach to Natural Products and Derivatives

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 3,6-Anhydro hexofuranose sugars are the structural motif of natural product furanodictines A–B and sauropunols A–D, F, and H. Conversion of the 2-hydroxyl group of alkyl-3,6-anhydro-5 -O- benzoyl- d -glucofuranosides to triflate intermediates followed by azidation reaction yielded 2-deoxy-2-azido derivatives when the substituents at C-1and C-2 are in cis relation; on the other hand, in the case of trans substituents, the products were α - glycosyl azide analogues. A similar reaction of butyl-3,6-anhydro-5 -O- benzoyl - d -mannofuranosides, obtained from the corresponding α- or β- d -glucofuranoside through appropriate oxidation and reduction reactions, yielded only 2-deoxy-2-azido products. We report here in a synthetic approach to 2-substituted sauropunols, furanodictines A–B, and related analogues, along with 1,4-disubstituted 1,2,3-triazolyl glycoconjugates and N -glycosyl amide starting from d -glucose derived precursors.

Source: ACS Omega

DOI: 10.1021/acsomega.5c05437