Synthesis of S-glycosyl thiophosphates, thiophosphonates and thiophosphinates by the Michaelis-Arbuzov rearrangement of anomeric thiocyanates.
Reaction of anomeric thiocyanates with a series of O-alkyl or O-trimethylsilyl phosphite, phenylphosphonite and diphenylphosphinite derivatives afforded the corresponding S-glycosyl thiophosphates, thiophosphonates and thiophosphinates in good yields. These derivatives had been previously applied as glycosyl donors in the synthesis of benzyl glycosides and disaccharides with excellent stereoselectivity.
Piekutowska
Marta
M
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland.
Pakulski
Zbigniew
Z
D006031:Glycosylation; D015394:Molecular Structure; D010710:Phosphates / Q000138:chemical synthesis* / Q000737:chemistry; D010720:Phosphines / Q000138:chemical synthesis* / Q000737:chemistry; D013861:Thiocyanates / Q000138:chemical synthesis* / Q000737:chemistry
D010710:Phosphates; D010720:Phosphines; D013861:Thiocyanates; C044646:phosphine; C035638:thiophosphoric acid