A convenient synthesis of glycosyl chlorides from sugar hemiacetals using triphosgene as the chlorine source.
Treating partially protected sugar hemiacetals with triphosgene in THF results in the formation of glycosyl chlorides. The method is compatible with acid-sensitive isopropylidene protecting groups in the hemiacetal substrates.
Cicchillo
R M
RM
Department of Chemistry, Youngstown State University, OH 44555-3663, USA.
Norris
P
P
D002241:Carbohydrates / Q000737:chemistry*; D002712:Chlorides / Q000138:chemical synthesis* / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010705:Phosgene / Q000031:analogs & derivatives* / Q000737:chemistry*
D002241:Carbohydrates; D002712:Chlorides; D005960:Glucosides; D010705:Phosgene; C111044:bis(trichloromethyl) carbonate