Synthesis of S-glycosyl thiophosphates, thiophosphonates and thiophosphinates by the Michaelis-Arbuzov rearrangement of anomeric thiocyanates

Carbohydr Res. 2008 Mar 17;343(4):785-92. doi: 10.1016/j.carres.2007.12.009. Epub 2007 Dec 23.

Abstract

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.

MeSH terms

  • Glycosylation
  • Molecular Structure
  • Phosphates / chemical synthesis*
  • Phosphates / chemistry
  • Phosphines / chemical synthesis*
  • Phosphines / chemistry
  • Thiocyanates / chemical synthesis*
  • Thiocyanates / chemistry

Substances

  • Phosphates
  • Phosphines
  • Thiocyanates
  • phosphine
  • thiophosphoric acid