86782-19-6

Upstream product

• 96291-87-1 (1S)-(1,4/2,3)-3,4-diacetoxy-5-<(benzoyloxy)methyl>-1,2-dibromocyclohex-5-ene 
• 74766-77-1 DL-di-O-acetyl-(1,3/2,4,6)-3,4-dibromo-6-benzoyloxymethyl-1,2-cyclohexanediol 
• 69982-70-3 3,4-di-O-acetyl-2,6-dibromo-2,6-dideoxy-5a-carba-β-DL-glucopyranosyl bromide 
• 74766-83-9 DL-1,2-di-O-acetyl-(1,4/2,3)-3,4-dibromo-6-bromomethyl-5-cyclohexene-1,2-diol 
• 74766-79-3 DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol 
• 74766-78-2 3,4-di-O-acetyl-1,5-anhydro-6-bromo-2,6-dideoxy-5a-carba-DL-arabino-hex-1-enitol 
• 532-32-1 sodium benzoate 
• 74766-84-0 DL-1,2-di-O-acetyl-(1,6/2,5)-3-benzoyloxymethyl-5,6-dibromo-3-cyclohexene-1,2-diol 
• 96291-86-0 (1R)-(1,3/2)-1,2-Di-O-acetyl-3-bromomethyl-5-cyclohexene-1,2-diol 
• 74766-83-9 Acetic acid (1S,2R,5S,6S)-2-acetoxy-5,6-dibromo-3-bromomethyl-cyclohex-3-enyl ester 
• 96291-85-9 (1R)-(1,3,5/2,4)-3,4-diacetoxy-1,2-dibromo-5-(bromomethyl)cyclohexane 
• 174966-55-3 (1R,2S,3S,4R,5R)-3-O-tert-butyldimethylsilyl-1-benzoyloxymethyl-4,5-O-cyclohexylidene-1,2,3,4,5-cyclohexanepentaol 
• 174966-54-2 (1R,2R,3S)-3-O-tert-butyldimethylsilyl-5-benzoyloxymethyl-1,2-O-cyclohexylidene-4-cyclohexen-1,2,3-triol 
• 203317-83-3 (1R,2R,3S,4R)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidene-5-cyclohexene-1,2,3,4-tetrol 

Downstream Products

• 71481-04-4 (2R)-trans-2,3-dihydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene 
• 96247-03-9 (2R)-trans-3-acetoxy-2-hydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene 
• 96247-02-8 (2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene 
• 86747-02-6 (+)-β-senepoxide 
• 96291-88-2 (1R)-3,4-di-O-acetyl-1,2-anhydro-(1,2,3/4)-5-<(benzoyloxy)methyl>-5-cyclohexene-1,2,3,4-tetrol 
• 96291-89-3 (1S)-3,4-di-O-acetyl-1,2-anhydro-(1,2,4/3)-5-<(benzoyloxy)methyl>-5-cyclohexene-1,2,3,4-tetrol 
• 17550-38-8 DL-3,4-di-O-acetyl-1,2-anhydro-(1,2/3,4)-2C-(benzoyloxymethyl)-5-cyclohexene-1,2,3,4-tetrol 
• 74766-86-2 D,L-(1,2,4/3)-3,4-di-O-acetyl-1,2-anhydro-5-benzoyloxymethyl-5-cyclohexene-1,2,3,4,-tetrol 
• 74766-86-2 DL-3,4-di-O-Acetyl-1,2-anhydro-(1,2,3/4)-5-benzoyloxymethyl-5-cyclohexene-1,2,3,4-tetrol 
• 20421-13-0 DL-5,6-di-O-acetyl-1,2:3,4-dianhydro-(1,2,6/3,4,5)-1-C-benzoyloxymethyl-1,2,3,4,5,6-cyclohexanehexol 
• 99232-71-0 (2R)-trans-2-acetoxy-3-<(E)-cinnamoyloxy>-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene 
• 99232-68-5 (2R)-trans-3-<(E)-cinnamoyloxy>-2-hydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene 

Relevant academic research and scientific papers

Enantiospecific syntheses of (+)-crotepoxide, (+)-boesenoxide, (+)-β- senepoxide, (+)-pipoxide acetate, (-)-iso-crotepoxide, (-)-senepoxide, and (- )-tingtanoxide from (-)-quinic acid

A convenient strategy that is ideally suited for the Construction of all the naturally occurring cyclohexane diepoxides and cyclohexene epoxides is described. The key intermediate 12, a 1,3-cyclohexadiene, has been prepared from (-)-quinic acid in 11 steps with 18% overall yield: Singlet oxygen photooxygenation of the 1,3-cyclohexadiene followed by rearrangement of the resultant endoperoxides with either cobalt-meso-tetraphenylporphyrin or trimethyl phosphite afforded enantiopure (+)-crotepoxide, (+)-boesenoxide, and (-)-iso-crotepoxide or (-)-senepoxide, (+)-β-senepoxide, (+)-pipoxide acetate, and (-)-tingtanoxide, respectively.

Total Synthesis of (+)-Pipoxide and (+)-β-Senepoxide and Their Diene Precursors

(2R)-trans-2,3-Diacetoxy-1-cyclohexa-4,6-diene (6), a diene precursor in the biosynthesis of highly oxygenated cyclohexane epoxides, has first been totally synthesized from the bromo lactone 16 derived from (1S)-endo-7-oxabicyclo2.2.1

SYNTHESIS AND EPOXIDATION OF TRANS-5,6-DIACETOXY-1-BENZOYLOXYMETHYL-1,3-CYCLOHEXADIENE.

The title substituted 1,3-cyclohexadiene was prepared in three steps from the readily available DL-1,2-di-O-acetyl-(1,3/2)-3-bromomethyl-5-cyclohexene-1,2-diol. Epoxidation of it with m-chloroperoxybenzoic acid in 1,2-dichloroethane afforded several stere

SYNTHESIS AND EPOXIDATION OF TRANS-5,6-DIACETOXY-1-BENZOYLOXYMETHYL-1,3-CYCLOHEXADIENE

Epoxidation of a newly prepared trans-5,6-diacetoxy-1-benzoyloxymethyl-1,3-cyclohexadiene by m-chloroperbenzoic acid in dichloroethane gave several isomeric compounds of the biologically important highly oxygenated cyclohexane derivatives.