An efficient route for the synthesis of glycosyl phosphinic acids.
An efficient method for the synthesis of glycosyl phosphinic acids (21) from the corresponding C-phosphonates is described. The route developed involves three steps: reduction of the glycosyl C-phosphonate to a primary phosphine, reaction of this product with an alkylating agent to afford a secondary phosphine, and finally oxidation to the phosphinic acid. Deprotection provides compounds suitable for testing as glycosyl phosphate analogues. Although the focus of this report is the synthesis of analogues of arabinofuranosyl-containing phosphate esters, the method should be readily applicable to other systems, carbohydrate or otherwise.
Centrone
Charla A
CA
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
Lowary
Todd L
TL
D002236:Carbohydrate Conformation; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010721:Phosphinic Acids / Q000138:chemical synthesis* / Q000737:chemistry
D006027:Glycosides; D010721:Phosphinic Acids