Ph2SO/Tf2O: a powerful promotor system in chemoselective glycosylations using thioglycosides.
Diphenylsulfoxide in combination with triflic anhydride provides a very potent thiophilic glycosylation promotor system, capable of activating disarmed thioglycosides. The usefulness of this novel thiophilic activator is illustrated in a successful chemoselective glycosylation sequence in which the donor thioglycoside in the first condensation step may be either armed or disarmed. [reaction: see text]
Codée
Jeroen D C
JD
Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Litjens
Remy E J N
RE
den Heeten
René
R
Overkleeft
Herman S
HS
van Boom
Jacques H
JH
van der Marel
Gijs A
GA
D000812:Anhydrides / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D002240:Carbohydrate Sequence; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013865:Thioglycosides / Q000737:chemistry*
D000812:Anhydrides; D001555:Benzene Derivatives; D009844:Oligosaccharides; D013865:Thioglycosides; C048860:diphenyl sulfoxide