N-(phenylthio)-epsilon-caprolactam: a new promoter for the activation of thioglycosides.
N-(phenylthio)-epsilon-caprolactam (1) has been applied as a new promoter for the activation of thioglycosides. This proceeds by the reaction of 1 with trifluoromethansulfonic anhydride, which subsequently activates the thioglycoside for glycosidic bond formation. Notably, the reaction proceeds efficiently at room temperature and is adaptable to our reactivity-based one-pot oligosaccharide synthesis. [reaction: see text]
Durón
Sergio G
SG
Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Polat
Tülay
T
Wong
Chi-Huey
CH
D002240:Carbohydrate Sequence; D006031:Glycosylation; D007769:Lactams / Q000737:chemistry*; D008969:Molecular Sequence Data; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
D007769:Lactams; D013440:Sulfides; D013865:Thioglycosides; C487233:N-(phenylthio)-epsilon-caprolactam