4.5 Article

Synthesis of fluorinated and nonfluorinated sugar alkenylphosphonates via highly stereoselective Horner-Wadsworth-Emmons olefination

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CARBOHYDRATE RESEARCH
卷 533, 期 -, 页码 -

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ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2023.108941

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Alkenylphosphonates; Carbohydrates; Fluorine; Horner-Wadsworth-Emmons olefination; Stereoselectivity

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New fluorinated and nonfluorinated sugar alkenylphosphonates were successfully synthesized using 1,2;5,6-di-O-iso-propylidene-alpha-D-glucofuranose as the starting material and Horner-Wadsworth-Emmons olefination as the key synthetic method. The resulting products exhibited exclusive or predominant E-stereochemistry.
New fluorinated and nonfluorinated sugar alkenylphosphonates were obtained. In all cases 1,2;5,6-di-O-iso-propylidene-alpha-D-glucofuranose was used as the starting material. The synthesis of alkenylphosphonates was based on Horner-Wadsworth-Emmons olefination. The process led to products with E-stereochemistry exclu-sively or predominately.

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