title: A practical and scalable synthesis of carbohydrate based oxepines.
abstract: An efficient, seven-step synthesis of carbohydrate based oxepines is reported using per-O-acetyl septanoses as key intermediates. The scope of the synthesis was evaluated by varying both the pyranose starting materials and protecting groups incorporated into the oxepine products. The practicality of the method make it amenable to scale up as demonstrated by the gram-scale synthesis of the d-glucose derived oxepine.
authors.affiliation: Department of Chemistry, University of Connecticut, 55 North Eagleville Road, U-3060, Storrs, CT 06269, USA. mark.peczuh@uconn.edu.
authors.forename: Raghu
authors.initials: R
authors.lastname: Vannam
authors.forename: Mark W
authors.initials: MW
authors.lastname: Peczuh
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D004148:Dioxolanes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D002241:Carbohydrates; D004148:Dioxolanes; D007659:Ketones; D010082:Oxepins