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(+)- and (-)-Benzopyrene 7,8-Oxide: Synthesis, Absolute Stereochemistry, and Stereochemical Correlation with Other Mammalian Metabolites of Benzopyrene

DOI: 10.1039/P19800002112

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2112 - 2116 (1980)

Update date:2022-09-26

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Authors:

Boyd, Derek R.Boyd, Derek R.

Gadaginamath, Guru S.Gadaginamath, Guru S.

Kher, AnilKher, Anil

Malone, John F.Malone, John F.

Yagi, HaruhikoYagi, Haruhiko

Jerina, Donald M.Jerina, Donald M.

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Article abstract of DOI:10.1039/P19800002112

Optically pure samples of (+)- and (-)-benzopyrene 7,8-oxide have been synthesized from the separated diastereisomers of trans-8-bromo-7-menthyloxyacetoxy-7,8,9,10-tetrahydrobenzopyrene.The latter separation was effected by short-column chromatography-recrystallisation or high pressure chromatography.The absolute stereochemistry of (+)-trans-8-bromo-7-menthyloxyacetoxy-7,8,9,10-tetrahydrobenzopyrene has been assigned as (7S,8S) by an X-ray crystal structure analysis; this structure has in turn been unequivocally correlated with the stereochemistry of (7S,8R)-(-)-benzopyrene 7,8-oxide and a range of mammalian metabolites.

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Product name:(+)-trans-8-bromo-7-menthyloxyacetoxy-7,8,9,10-tetrahydrobenzopyrene

Cas No:68906-74-1

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