Direct preparation of nucleoside vinyl disulfides from 2-(trimethylsilyl)ethyl sulfides, an access to vinylthiols.
We report here a straightforward preparation of various nucleoside vinyl disulfides in high yields under mild conditions using the new reaction of vinyl 2-(trimethylsilyl)ethyl (TMSE) sulfides with sulfenyl chlorides. This reaction allows the preparation of various mixed disulfides from stable silyl sulfides without formation of oxidizable and/or unstable thiols. The easy preparation of vinyl disulfides through this reaction should offer new perspectives in vinylthiol chemistry.
Gerland
Béatrice
B
Département de Pharmacochimie Moléculaire, UMR 5063 CNRS/Université Joseph Fourier-Grenoble I, ICMG FR CNRS 2607, F-38041 Grenoble, France.
Désiré
Jérôme
J
Lepoivre
Michel
M
Décout
Jean-Luc
JL
D002384:Catalysis; D004220:Disulfides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013440:Sulfides / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D004220:Disulfides; D009705:Nucleosides; D012821:Silanes; D013438:Sulfhydryl Compounds; D013440:Sulfides; D014753:Vinyl Compounds