Stereoselective synthesis of a C-glycoside analogue of N-Fmoc-serine beta-N-acetylglucosaminide by Ramberg-Bäcklund rearrangement.
A C-glycoside analogue of N-Fmoc-serine beta-N-acetylglucosaminide 1 was synthesized stereoselectively from a sulfone derivative of serinol thio-N-acetylglucosamide 8 using a Ramberg-Bäcklund rearrangement as a key step.
Ohnishi
Yuki
Y
Department of Pharmacology and Molecular Sciences, Johns Hopkins University School of Medicine, Baltimore, MD 21205, USA.
Ichikawa
Yoshitaka
Y
D000117:Acetylglucosamine / Q000737:chemistry*; D006027:Glycosides; D008968:Molecular Conformation; D015335:Molecular Probes / Q000138:chemical synthesis* / Q000737:chemistry; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism
C438934:C-glycoside; D006027:Glycosides; D015335:Molecular Probes; D009005:Monosaccharides; D012694:Serine; D000117:Acetylglucosamine