Formation of beta-glucosamine and beta-mannose linkages using glycosyl phosphates.
[reaction: see text] Glycosyl phosphates were examined for their utility in the synthesis of challenging glycosidic linkages. beta-Glucosamine glycosides were formed preferentially and in good yield. beta-Mannosides were constructed in high overall yield with modest anomeric selectivity. Interesting solvent and conformational influences on the stereochemical outcome of the coupling reactions were observed.
Plante
O J
OJ
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Palmacci
E R
ER
Seeberger
P H
PH
D000097:Acetonitriles; D005944:Glucosamine / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000737:chemistry*; D008362:Mannosides / Q000138:chemical synthesis; D008968:Molecular Conformation; D010755:Organophosphates / Q000737:chemistry*
D000097:Acetonitriles; D006027:Glycosides; D007202:Indicators and Reagents; D008362:Mannosides; D010755:Organophosphates; D005944:Glucosamine; D008358:Mannose; C032159:acetonitrile