A straightforward alpha-selective aromatic glycosylation and its application for stereospecific synthesis of 4-methylumbelliferyl alpha-T-antigen.
A practical and efficient alpha-selective aromatic glycosylation with simple per-O-acetyl glycopyranosyl trichloroacetimidates is reported. The method is particularly effective for L-fucosyl and 2-azido-2-deoxy-D-galatosaminyl imidates, with which exclusive alpha-selectivity was achieved. The synthetic utility of this method was demonstrated in the stereoselective synthesis of 4-methylumbelliferyl alpha-T-antigen.
Chang
Shih-Sheng
SS
Department of Applied Chemistry, National Chiao Tung University, Taiwan, ROC.
Lin
Chun-Cheng
CC
Li
Yaw-Kuen
YK
Mong
Kwok-Kong Tony
KK
D000081:Acetamides; D000957:Antigens, Viral, Tumor / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D062845:Chloroacetates; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D007096:Imidoesters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013237:Stereoisomerism; D014238:Trichloroacetic Acid / Q000737:chemistry
D000081:Acetamides; D000957:Antigens, Viral, Tumor; D062845:Chloroacetates; D006020:Glycopeptides; D007096:Imidoesters; D014238:Trichloroacetic Acid; C009528:trichloroacetamide