Short synthesis of enantiopure C2-symmetric 1,2:4,5-diepoxypentane and "pseudo"-C2-symmetric 3-azido-1,2:4,5-diepoxypentane from arabitol.
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.
Boydell
A James
AJ
Department of Chemistry, Southampton University, Highfield, Southampton SO17 1BJ, UK.
Jeffery
Martin J
MJ
Bürkstümmer
Eva
E
Linclau
Bruno
B
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*
C482093:3-azido-1,2-4,5-diepoxypentane; D001386:Azides; D004852:Epoxy Compounds; D013402:Sugar Alcohols; C012898:1,2,4,5-diepoxypentane; C014999:arabitol