63268-38-2

Upstream product

• 169437-81-4 trans-(7R,8R)-7,8-dibenzoyloxy-7,8,9,10-tetrahydrobenzopyrene 
• 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 
• 17573-15-8 9,10-dihydro benzopyrene 
• 532-31-0 silver benzoate 
• 6272-55-5 7-hydroxy-7,8,9,10-tetrahydrobenzopyrene 
• 57405-01-3 C₃₄H₂₃BrO₄ 
• 57405-00-2 (+/-)-7,8,9,10-Tetrahydrobenzopyrene-trans-7,8-diol dibenzoate 
• 36504-67-3 7,8-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 

Downstream Products

• 57404-88-3 (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene 
• 60864-95-1 (-)-7R-trans-Benzopyrene-7,8-dihydrodiol 
• 62314-67-4 (+/-)-trans-7,8-Dihydrobenzo[a]pyrene-7,8-diol 
• 922168-07-8 C₂₀H₁₂(OC(O)C₆H₅)2(O₂BC₆H₅) 
• 63323-31-9 (-)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 62697-16-9 (+/-)-7β,8α,9α,10α-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 486420-76-2 N⁶-[10α*-(7α*,8β*,9β*-trisbenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-4',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 
• 486420-73-9 N²-[10-(7,8,9-trisbenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine 

Relevant academic research and scientific papers

Enantioselective Synthesis of the (+)-anti-7,8-Dihydrodiol-9,10-epoxide of the Potent Carcinogen Benzopyrene

The title compound, the most important genotoxic metabolite of benzopyrene, has been prepared efficiently in a synthesis which capitalized on Jacobsen-type enantioselective epoxidation of 9,10-dihydrodibenzopyrene, cleavage of the epoxide by KOH-Me2SO to give the tetrahydro-trans-7,8-diol, and formation of the dibenzoate from which the contaminating antipode was removed by crystallization.

Enantioselective synthesis of the tumorigenic anti-diol epoxide metabolites of benzo[a]pyrene

Efficient, highly enantioselective syntheses of (+) and (-)-anti-benzo[a]pyrene diol epoxide (BPDE) from 9,10-dihydrobenzo[a]pyrene are described. Initial epoxidation catalyzed by (salen) Mn(III) complex gives 7,8-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (

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.