SmI2-mediated reactions of diethyl iodomethylphosphonate with esters and lactones: a highly stereoselective synthesis of a precursor of the C-glycosyl analogue of thymidine 5′-(β-l-rhamnosyl)diphosphate

✍ Scribed by Fulvia Orsini; Alessandro Caselli

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 196 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)01540-x

✦ Synopsis

In the presence of samarium iodide diethyl iodomethylphosphonate reacts with esters to afford b-ketophosphonates. The protocol has been applied to sugar lactones to afford in fairly good yields intermediates that are useful precursors for a variety of potentially bioactive compounds, such as the C-glycosyl analogue of thymidine 5%-(b-L-rhamnosyl)diphosphate.