title: β-Stereoselective phosphorylations applied to the synthesis of ADP- and polyprenyl-β-mannopyranosides.
abstract: An efficient and convenient synthetic route to glycosyl 1-β-phosphates has been developed using diallyl chlorophosphate as a phosphorylating agent with 4-N,N-dimethylaminopyridine under mild conditions. Diallyl-glycosyl 1-β-phosphate triesters of D-manno, L-glycero-D-manno-hepto-, D-gluco-, D-galacto-, and L-fuco-pyranose as well as lactose have been obtained by this strategy in good yields and excellent β-selectivities. Furthermore, the diallyl 6-azido-mannosyl 1-β-phosphate 2 was deprotected under mild conditions and converted into potentially clickable analogues of β-mannosyl phosphoisoprenoids I and ADP-heptose II.
authors.affiliation: Département de Chimie, Laboratoire de Chimie Bio-Organique, University of Namur , rue de Bruxelles 61, B-5000 Namur, Belgium.
authors.forename: Tianlei
authors.initials: T
authors.lastname: Li
authors.forename: Abdellatif
authors.initials: A
authors.lastname: Tikad
authors.forename: Weidong
authors.initials: W
authors.lastname: Pan
authors.forename: Stéphane P
authors.initials: SP
authors.lastname: Vincent
mesh_terms: D000244:Adenosine Diphosphate / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D006539:Heptoses / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010766:Phosphorylation; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D006539:Heptoses; C062615:glycero-alpha-manno-heptopyranose; D000244:Adenosine Diphosphate