Highly stereoselective synthesis of alpha-D-mannopyranosyl phosphosugars.
Alpha-mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thioglycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.
Crich
David
D
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette, France. dcrich@icsn.cnrs-gif.fr
Picard
Sébastien
S
D000812:Anhydrides / Q000737:chemistry; D001597:Benzylidene Compounds / Q000737:chemistry; D008360:Mannosephosphates / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry
C469850:1-(benzenesulfinyl)piperidine; D000812:Anhydrides; D001597:Benzylidene Compounds; D008360:Mannosephosphates; D008698:Mesylates; D010880:Piperidines; D011743:Pyrimidines; D000644:Quaternary Ammonium Compounds; D013865:Thioglycosides; C012077:trifluoromethanesulfonic acid; C030986:pyrimidine