Glycosylation using a one-electron-transfer, homogeneous reagent. Application to an efficient synthesis of the trimannosyl core of N-glycosylproteins.
Double glycosylation of methyl 2,4-di-O-benzyl-beta-D-mannopyranoside with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-alpha-D-mannopyranoside using as promoter tris(4-bromophenyl)ammoniumyl hexachloroantimonate, a stable, commercial, and crystalline radical cation, afforded after debenzoylation methyl 2,4-di-O-benzyl-3,6-di-O-(3,4,6-tri-O-benzyl-alpha-D-mannopyranoside in excellent yield. Other mannosyl donors were also investigated.
Zhang
Y M
YM
Ecole Normale Supérieure, Laboratoire de Chimie, U.R.A. 1110, Paris, France.
Mallet
J M
JM
Sinaÿ
P
P
D002240:Carbohydrate Sequence; D004579:Electron Transport; D006031:Glycosylation; D007202:Indicators and Reagents; D008358:Mannose / Q000737:chemistry*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009942:Organometallic Compounds; D011506:Proteins / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds; D014312:Trisaccharides / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D009942:Organometallic Compounds; D011506:Proteins; D000644:Quaternary Ammonium Compounds; D014312:Trisaccharides; C079938:tris(4-bromophenyl)ammoniumyl hexachloroantimonate; D008358:Mannose