title: Short synthesis of enantiopure C2-symmetric 1,2:4,5-diepoxypentane and "pseudo"-C2-symmetric 3-azido-1,2:4,5-diepoxypentane from arabitol.
abstract: On the basis of our previously described selective protection of arabitol as its 1,2:4,5-bis-pentylidene acetal 5, we report a straightforward synthesis of the novel "pseudo"-C(2)-symmetric 3-azido-1,2:4,5-diepoxypentane building block 4 in 6 steps from arabitol. Using a similar synthetic route, an improved synthesis of the C(2)-symmetrical 1,2:4,5-bis-epoxypentane building block 1 is described, also in 6 steps from arabitol. Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis.
authors.affiliation: Department of Chemistry, Southampton University, Highfield, Southampton SO17 1BJ, UK.
authors.forename: A James
authors.initials: AJ
authors.lastname: Boydell
authors.forename: Martin J
authors.initials: MJ
authors.lastname: Jeffery
authors.forename: Eva
authors.initials: E
authors.lastname: Bürkstümmer
authors.forename: Bruno
authors.initials: B
authors.lastname: Linclau
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000737:chemistry*
chemical_list: C482093:3-azido-1,2-4,5-diepoxypentane; D001386:Azides; D004852:Epoxy Compounds; D013402:Sugar Alcohols; C012898:1,2,4,5-diepoxypentane; C014999:arabitol