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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

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
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
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.
2-directional chain synthesis, efficient synthesis, desymmetrization, deoxygenation, construction, inhibitors, precursors, metathesis, chemistry
0022-3263
8252-8255
Boydell, A. J.
e06d686e-b65b-49c2-a45a-117e2d380ae3
Jeffery, M. J.
93c5fbd6-ccac-4267-a452-89cf70fd2101
Burkstummer, E.
925a29e7-b0c8-4589-bfe7-52a9d851003a
Linclau, B.
19b9cacd-b8e8-4c65-af36-6352cade84ba
Boydell, A. J.
e06d686e-b65b-49c2-a45a-117e2d380ae3
Jeffery, M. J.
93c5fbd6-ccac-4267-a452-89cf70fd2101
Burkstummer, E.
925a29e7-b0c8-4589-bfe7-52a9d851003a
Linclau, B.
19b9cacd-b8e8-4c65-af36-6352cade84ba

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), 8252-8255. (doi:10.1021/jo034374x).

Record type: Article

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 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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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: https://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: 06 Jun 2018 12:52

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