title: Application of bis(diphenylphosphino)ethane (DPPE) in Staudinger-type N-glycopyranosyl amide synthesis.
abstract: Bis(diphenylphosphino)ethane (DPPE) reacts with pyranosyl azides derived from D-glucose and D-glucuronic acid in the presence of acid chlorides to yield the corresponding glycosyl amides. Reaction rates are comparable to those with triphenylphosphine, however, the byproduct phosphine oxide is easily removed from reaction mixtures using column chromatography. The simple and clean workup allows for the formation of collections of related compounds by parallel synthesis, and the method is also applicable to scaled-up reactions. The beta-stereochemistry of the glycosyl azide precursor is retained in all cases, which is supported by X-ray crystallography in several cases.
authors.affiliation: Department of Chemistry, Youngstown State University, 1 University Plaza, Youngstown, OH 44555, USA.
authors.forename: David P
authors.initials: DP
authors.lastname: Temelkoff
authors.forename: Craig R
authors.initials: CR
authors.lastname: Smith
authors.forename: Daniel A
authors.initials: DA
authors.lastname: Kibler
authors.forename: Shawn
authors.initials: S
authors.lastname: McKee
authors.forename: Sara J
authors.initials: SJ
authors.lastname: Duncan
authors.forename: Matthias
authors.initials: M
authors.lastname: Zeller
authors.forename: Mo
authors.initials: M
authors.lastname: Hunsen
authors.forename: Peter
authors.initials: P
authors.lastname: Norris
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis*
chemical_list: D000577:Amides; D009943:Organophosphorus Compounds; D011714:Pyrans; C049078:bis(diphenylphosphine)ethane