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

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.

Automated summary

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.