title: A versatile route to L-hexoses: synthesis of L-mannose and L-altrose.
abstract: [reaction: see text] An efficient route for the synthesis of orthogonally protected l-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-l-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-l-pyranoside, which can be suitably functionalized to afford the desired l-hexoses. In this paper, we report the synthesis of l-manno- and l-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.
authors.affiliation: Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, via Cynthia, 4 I-80126 Napoli, Italy. guaragna@unina.it
authors.forename: Annalisa
authors.initials: A
authors.lastname: Guaragna
authors.forename: Carmela
authors.initials: C
authors.lastname: Napolitano
authors.forename: Daniele
authors.initials: D
authors.lastname: D'Alonzo
authors.forename: Silvana
authors.initials: S
authors.lastname: Pedatella
authors.forename: Giovanni
authors.initials: G
authors.lastname: Palumbo
mesh_terms: D002384:Catalysis; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006601:Hexoses; D008358:Mannose