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Short synthesis of enantiopure C-2-Symmetric 1,2 : 4,5-diepoxypentane and "Pseudo"-C-2-symmetric 3-azido-1,2 : 4,5-diepoxypentane from arabitol

Record type: Article

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 I 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.

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Citation

Boydell, A. J., Jeffery, M. J., Burkstummer, E. and Linclau, B. (2003) Short synthesis of enantiopure C-2-Symmetric 1,2 : 4,5-diepoxypentane and "Pseudo"-C-2-symmetric 3-azido-1,2 : 4,5-diepoxypentane from arabitol Journal of Organic Chemistry, 68, (21), pp. 8252-8255. (doi:10.1021/jo034374x).

More information

Published date: 17 October 2003
Keywords: 2-directional chain synthesis, efficient synthesis, desymmetrization, deoxygenation, construction, inhibitors, precursors, metathesis, chemistry

Identifiers

Local EPrints ID: 19912
URI: http://eprints.soton.ac.uk/id/eprint/19912
ISSN: 0022-3263
PURE UUID: 7fb249b1-2bb3-4b8a-adbe-2a920efb4340
ORCID for B. Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 20 Feb 2006
Last modified: 17 Jul 2017 16:30

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Contributors

Author: A. J. Boydell
Author: M. J. Jeffery
Author: E. Burkstummer
Author: B. Linclau ORCID iD

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