A novel synthesis of D-galactofuranosyl, D-glucofuranosyl and D-mannofuranosyl 1-phosphates based on remote activation of new and free hexofuranosyl donors.
The selective synthesis of 1,2-cis-hexofuranosyl 1-phosphates was readily accomplished according to a procedure based on the 'Remote Activation Concept'. This approach required (i) the preparation of suitable 1,2-trans-hexofuranosyl donors, so that new heterocyclic thiofuranosides were designed and synthesized, (ii) the stereocontrolled phosphorylation of the corresponding unprotected donors and (iii) the simple and fast purification of the resulting anomeric phosphates. This approach showed to be equally efficient in the galactose, glucose and mannose series.
Ferrières
Vincent
V
Ecole Nationale Supérieure de Chimie de Rennes, UMR CNRS 6052 Synthèses et Activations de Biomolécules, Institut de Chimie de Rennes, Avenue du Général Leclerc, France. vincent.ferrieres@ensc-rennes.fr
Blanchard
Sophie
S
Fischer
Delphine
D
Plusquellec
Daniel
D
D005695:Galactosephosphates / Q000138:chemical synthesis; D005958:Glucosephosphates / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis; D008360:Mannosephosphates / Q000138:chemical synthesis; D010766:Phosphorylation; D013237:Stereoisomerism; D013403:Sugar Phosphates / Q000138:chemical synthesis*; D013865:Thioglycosides / Q000737:chemistry
D005695:Galactosephosphates; D005958:Glucosephosphates; D006027:Glycosides; D008360:Mannosephosphates; D013403:Sugar Phosphates; D013865:Thioglycosides; C029973:galactose-1-phosphate; C047217:mannose 1-phosphate; C031590:glucose-1-phosphate