title: Synthesis of lemonose derivatives: methyl 4-amino-3-O,4-N-carbonyl-2,4,6-trideoxy-3-C-methyl-α-l-lyxo-pyranoside and its phenyl thioglycoside.
abstract: Lemonose is a component of the antibiotic lemonomycin and other antibiotics and natural products. Three routes to the synthesis of the title compound, a protected, desmethyl derivative of lemonose, from l-rhamnose or its glycal, were investigated based on electrophilic cyclization, epoxidation-ring opening, and deoxygenation of an intermediate that was used in the synthesis of the amino sugar callipeltose. The deoxygenation route was successful and it provided the title compound, which was then converted to a phenyl thioglycoside.
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, United States.
authors.forename: Alicia C
authors.initials: AC
authors.lastname: Briegel
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, United States.
authors.forename: Adrienne K
authors.initials: AK
authors.lastname: Cummings
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, United States.
authors.forename: Garry R
authors.initials: GR
authors.lastname: Smith
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, United States.
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Doroski
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, United States.
authors.forename: Walter J
authors.initials: WJ
authors.lastname: Boyko
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, United States.
authors.forename: Nicholas A
authors.initials: NA
authors.lastname: Piro
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, United States.
authors.forename: W Scott
authors.initials: WS
authors.lastname: Kassel
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, United States. Electronic address: robert.giuliano@villanova.edu.
authors.forename: Robert M
authors.initials: RM
authors.lastname: Giuliano
mesh_terms: D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D006027:Glycosides; D013865:Thioglycosides
keywords: Callipeltose; Lemonomycin; Lemonose