69945-44-4

Usage

Uses

Used in Organic Synthesis:
(1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol is used as a key intermediate in organic synthesis for the preparation of other organic compounds. Its unique structure with bromine atoms and hydroxyl groups allows for versatile reactions and the formation of a wide range of products.
Used in Chemical Reactions as a Reagent:
In the field of chemical reactions, (1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol serves as a reagent, facilitating various organic transformations. Its presence can enhance the efficiency and selectivity of certain reactions, making it a valuable tool in chemical research and development.
Used in the Study of Organic Chemical Reactions:
(1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol is also utilized in academic and research settings to study the mechanisms and kinetics of organic chemical reactions. Its distinct structure provides insights into reaction pathways and helps in understanding the behavior of similar compounds.
It is crucial to handle (1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol with care, as it may pose hazards if not used properly, highlighting the importance of safety precautions in its applications.

Upstream product

• 5273-61-0 (5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione 
• 106-51-4 p-benzoquinone 

Downstream Products

• 169529-93-5 (-)-2,3-dibromocyclohex-5-ene-1,4-diol 
• 170210-90-9 Acetic acid (1R,4R,5S,6S)-4-acetoxy-5,6-dibromo-cyclohex-2-enyl ester 
• 4381-96-8 (+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol 
• 87160-88-1 DL-(1α,2α,5α,6α)-5-<(4-Methylphenylsulfonyl)amino>-7-oxabicyclo<4.1.0>hept-3-en-2-ol 
• 112346-61-9 DL-(1α,2α,3β,6β)-2-Brom-6-<(4-methylphenylsulfonyl)amino>-4-cyclohexen-1,3-diol 
• 87160-99-4 N-((1S,2R,3S,6R)-3-Methoxy-7-oxa-bicyclo[4.1.0]hept-4-en-2-yl)-4-methyl-benzenesulfonamide 
• 76670-75-2 DL-(1α,2β,4β,7α)-8-(4-Methylphenylsulfonyl)-3-oxa-8-azatricyclo<5.1.0.0^2,4>oct-5-en 
• 5273-61-0 trans-5,6-Dibrom-cyclohex-2-en-1,4-dion 
• 18376-35-7 (1α,2β,3α,4β,5β,6β)-1,2-dibromo-3,4,5,6-tetraacetoxycyclo-hexane 
• 18376-35-7 (1α,2β,3α,4α,5β,6β)-1,2-dibromo-3,4,5,6-tetraacetoxycyclohexane 
• 145047-67-2 Acetic acid (1R,2S,3S,4R,5S,6R)-4-acetoxy-2,3-dibromo-5,6-dihydroxy-cyclohexyl ester 
• 18376-36-8 (1S,2S,3S,4S,5R,6R)-5,6-Dibromo-cyclohexane-1,2,3,4-tetraol 
• 4381-96-8 (+/-)-tetraacetylconduritol C 
• 4381-96-8 (+/-)-1,2,3,4-tetra-O-acetylconduritol E 

Relevant academic research and scientific papers

Highly Functionalized Cyclohexenyl Systems: Enzymatic Resolution and Selective Oxirane Opening Reactions of p-Benzoquinone Derivatives

Diol 2, derived in two steps from p-benzoquinone, was converted to epoxy alcohol 3. The latter was resolved with crude Candida rugosa lipase in isopropenyl acetate/toluene to give acetate (-)-4 and residual alcohol (+)-3. Oxirane ring opening reactions of 3 and the corresponding acetate and TBDMS derivatives with a variety of nucleophiles gave diastereomerically pure 3,4,5,6-tetrasubstituted cyclohexene derivatives of type 6. X-ray crystal structures were obtained on compounds 6e, 6m and the diacetate prepared from 61. Nitrogen nucleophiles provided entry in various aziridines 10. Pd(0)-catalyzed nucleophilic additions to substrate 5 cleanly provided the diastereomeric pattern of type 11. trans-5,6-Disubstituted cyclohexadienes 13 were obtained by an unusual syn-reductive elimination on bromocarbonates 12 utilizing Pd or Zn.

Concise syntheses and some biological activities of dl-2,5-di-O-methyl-chiro-inositol, dl-1,4-di-O-methyl-scyllo-inositol, and dl-1,6-dibromo-1,6-dideoxy-2,5-di-O-methyl-chiro-inositol

The regio- and stereospecific synthesis of O-methyl-chiro-inositols and O-methyl-scyllo-inositol was achieved, starting from p-benzoquinone. After preparing dimethoxy conduritol-B as a key compound, regiospecific bromination of the alkene moiety of dimeth

Regio- and stereospecific synthesis of DL-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol

The regio- and stereospecific synthesis of DL-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol is reported. Bromination of p-benzoquinone followed by reduction of the carbonyl groups with NaBH4 gave the corresponding trans-dibromodiol compou

Synthesis of novel mono and bis-indole conduritol derivatives and their α/β-glycosidase inhibitory effects

Here we synthesized four novel indole conduritol derivatives 1-4 for the first time in the literature and probed their biological activities with the α and β-glucosidases. The compounds showed quite effective glucosidase inhibitory action. IC50

Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4

A variety of novel cyano-cyclitols possessing complex stereochemistry have been synthesized. These compounds were subjected to the biocatalyzed hydrolysis of their nitrile groups. The bacterial strain Rhodococcus erythropolis A4, expressing a nitrile hydr

A novel chemo-multienzymatic synthesis of bioactive cyclophellitol and epi-cyclophellitol in both enantiopure forms

A new route to synthesize cyclophellitol and epi-cyclophellitol from racemic starting materials in enantiopure forms has been developed. The synthesis involves a multi-enzymatic biotransformation pathway of the novel cyano-cyclitol (1R,4S,5R,6R)/(1S,4R,5S

Asymmetric induction of conduritols via AAA reactions: Synthesis of the aminocyclohexitol of hygromycin A

Two synthetic routes towards the construction of the aminocyclohexitol moiety of hygromycin A have been developed based on palladium-catalyzed asymmetric alkylation of conduritol derivatives. A protocol has been established whereby this biologically relev

Enantioselective synthesis of (-)-LL-C10037α from benzoquinone

(formula presented) The enantioselective total synthesis of the Streptomyces metabolite (-)-LL-C10037α has been accomplished in 10 steps and 20% overall yield. An early chiral intermediate was resolved with Candida rugosa lipase to provide (+)-5 with an e

Enzyme-assisted total synthesis of the optical antipodes D-myo-inositol 3,4,5-trisphosphate and D-myo-inositol 1,5,6-trisphosphate: Aspects of their structure-activity relationship to biologically active inositol phosphates

Unambiguous total syntheses of both optical antipodes of the enantiomeric pair D-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P3) and D- myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P3) are described. The ring system characteristic of