Synthesis of thiapyranoside precursors using the building-block approach from a phosphonodifluorodithioacetate

✍ Scribed by Emmanuel Pfund; Thierry Lequeux; Michel Vazeux; Serge Masson

• Book ID: 104250628
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 186 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00204-6

✦ Synopsis

Phosphonodifluorodithioacetate 2 demonstrates high reactivity towards dienes due to the presence of the two fluorine atoms. A hetero Diels-Alder reaction afforded the corresponding dihydrothiapyrans in 60-90% yields. These adducts can be submitted to a selective dihydroxylation and desulfanylation to produce phosphonodifluorothiaglycoside precursors.