The Michaelis-Arbuzov rearrangement of anomeric thiocyanates: synthesis and application of S-glycosyl thiophosphates, thiophosphonates and thiophosphinates as glycosyl donors

Reaction of anomeric thiocyanates with triethyl phosphite, dimethyl phenylphosphonite and methyl diphenylphosphinite afforded the corresponding S-glycosyl thiophosphates, thiophosphonates and thiophosphinates in good yields. These derivatives were applied as glycosyl donors in the synthesis of benzyl glycosides and disaccharides with excellent stereoselectivity.