57405-00-2

Usage

Uses

Used in the preparation of carcinogenic Benzo[a]pyrene Diol Epoxide (B287550).

Upstream product

• 6272-55-5 7-hydroxy-7,8,9,10-tetrahydrobenzopyrene 
• 17573-15-8 9,10-dihydro benzopyrene 
• 532-31-0 silver benzoate 

Downstream Products

• 57405-01-3 C₃₄H₂₃BrO₄ 
• 63323-31-9 (-)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 60864-95-1 (-)-7R-trans-Benzopyrene-7,8-dihydrodiol 
• 62314-67-4 (+/-)-trans-7,8-Dihydrobenzo[a]pyrene-7,8-diol 
• 63323-30-8 (7R,8S)-dihydroxy-(9S,10R)-epoxy-7,8,9,10-tetrahydrodibenzo[a]pyrene 
• 63268-35-9 trans-(7S,8S)-7,8-dibenzoyloxy-7,8,9,10-tetrahydrobenzopyrene 
• 169437-81-4 trans-(7R,8R)-7,8-dibenzoyloxy-7,8,9,10-tetrahydrobenzopyrene 
• 63268-37-1 C₃₄H₂₂O₄ 
• 63268-38-2 7,8-bis-benzoyloxy-7,8-dihydro benzo[a]pyrene 
• 57404-88-3 (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene 
• 57405-08-0 (+/-)-trans-7,8-Dihydrobenzopyrene-7,8-diol dibenzoate 
• 63227-55-4 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (7S,8S)-8-hydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-7-yl ester 
• 63268-36-0 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (7R,8R)-8-hydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-7-yl ester 

Relevant academic research and scientific papers

Improved Formal Preparation of Enantiomerically Pure anti-Benzopyrene Diol Epoxide.

We report an improved, economical formal route to enantiomerically pure anti-benzopyrene diol epoxide (BPDE).A trimethylaluminum catalyzed regio- and stereoselective opening of racemic 7,8-epoxy-7,8,9,10-tetrahydrobenzopyrene with Mosher's acid delivers benzylic esters exclusively.This step is a significant improvement over the lack of regioselectivity of standard procedures.We also show that modification of the subsequent chemical steps further shortens the preparation of enantiomerically pure anti-BPDE.

Preparation of Enantiomers of (+/-)-trans-7β,8α-Dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzopyrene

(+/-)-trans-7,8-Dihydroxy-7,8-dihydrobenzopyrene (VII), obtained from 7,8,9,10-tetrahydrobenzopyrene-7(8H)-one (I) by modifications and improvements of the reported procedures, has been converted into its di-(-) and (+)-menthoxyacetate derivatives in 82percent yield.The diastereomers have been separated by liquid chromatography on Lichrosorp Si 60 (30μ) column (100 cm x 1 cm dia.) using methylene chloride-ethyl acetate (99.4/0.6, v/v) as eluant.The enantiomers are liberated from the separated diastereomers by methanolysis with catalytic amount of sodium methoxide and converted into the enantiomers of (+/-)-trans-7β,8α-dihydroxy- 9α,10α-epoxy-7,8,9,10-tetrahydrobenzopyrene by m-chloroperbenzoic acid in an overall yield of 30percent.The CD and the UV spectra of the diastereomers and the enantiomers are reported.