455330-42-4

Upstream product

• 1370320-08-3 (+)-tert-butyl (1R,4S)-2-bromo-4-hydroxycyclohex-2-enylcarbamate 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 
• 108-86-1 bromobenzene 
• 174817-06-2 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohex-3-ene 
• 77300-23-3 cyclohex-(±)-(1R*,4S*)-2-ene-1,4-diyl dibenzoate 
• 217438-72-7 1R,4S-(4-hydroxycyclohex-2-enyl)carbamic acid tert-butyl ester 
• 1370320-04-9 (+)-tert-butyl N-[(1R,4S)-2-bromo-4-[(tert-butyldimethylsilyl)oxy]cyclohex-2-en-1-yl]carbamate 
• 1370320-03-8 C₁₃H₂₄BrNO₃Si 
• 455330-48-0 (1R,2S)-2-acetoxy-5,5-ethylenedioxycyclohexane carboxylic acid 
• 685087-25-6 (7R,8S)-8-Hydroxy-1,4-dioxa-spiro[4.5]decane-7-carboxylic acid 
• 455330-49-1 (1S)-4,4-ethylenedioxy-2-iodo-1-cyclohexyl acetate 
• 532989-56-3 Acetic acid (S)-(1,4-dioxa-spiro[4.5]dec-6-en-8-yl) ester 
• 1025922-65-9 (R)-8-Azido-1,4-dioxa-spiro[4.5]dec-6-ene 
• 455330-50-4 (1S)-4,4-ethylenedioxy-2-cyclohexen-1-ol 

Downstream Products

• 1316755-69-7 (2S)-2-{(1R,3S,4R)-4-[bis(3-methylbutyl)amino]-3-[4-(trifluoromethyl)phenyl]cyclohexyl}propanoic acid 
• 1316755-68-6 (2R)-2-{(1R,3S,4R)-4-[bis(3-methylbutyl)amino]-3-[4-(trifluoromethyl)phenyl]cyclohexyl}propanoic acid 
• 140111-52-0 epibatidine 

Relevant academic research and scientific papers

Scalable Asymmetric Synthesis of the All Cis Triamino Cyclohexane Core of BMS-813160

BMS-813160 is a pharmaceutical entity currently in development at Bristol Myers Squibb. Its defining structural feature is a unique chiral all cis triamino cyclohexane core. Medicinal and process chemistry groups at BMS have previously published synthesis

Asymmetric stereodivergent strategy towards aminocyclitols

A concise asymmetric synthesis of aminocyclitols, such as diastereomeric 2-deoxystreptamine analogues and conduramine A, is described. The Pd-catalyzed asymmetric desymmetrization of meso 1,4-dibenzolate enables the synthesis of highly oxidized cyclohexane architectures. These scaffolds can potentially be used to access new aminoglycoside antibiotics and enantiomerically pure α-glucosidase inhibitors.

Chemoenzymatic formal synthesis of (-)- and (+)-epibatidine

The cis-dihydrocatechol, derived from enzymatic cis-dihydroxylation of bromobenzene using the microorganism Pseudomonas putida UV4, was converted into (-)-epibatidine in eleven steps with complete stereocontrol. In addition, an unprecedented palladium-catalysed disproportionation reaction gave the (+)-enantiomer of an advanced key intermediate employed in a previous synthesis of epibatidine.

Enantioselective synthesis of (-)-N-Boc-7-azabicyclo-[2.2.1]heptan-2-one and (+)-N-Boc-4-amino-2-cyclohexen-1-one: Formal total synthesis of both enantiomers of epibatidine

We succeeded in the stereoselective synthesis of (-)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one ((-)-2) and (+)-N-Boc-4-amino-2-cyclohexen-1-one ((+)-3), key intermediates to (-) and (+)-epibatidine from a common chiral building block ethyl (1R,2S)-5,5-ethylen

α-iodocycloalkenones: Synthesis of (±)-epibatidine

A synthesis of the non-opiate analgesic alkaloid epibatidine was achieved in 13 steps and 13% Overall yield starting from 1,3-cyclohexadiene using in a key step a modified Stille coupling reaction on an α- iodocyclohexenone.

An asymmetric synthesis (-)-epibatidine

A Pd catalyzed desymmetrization of cis-3,6-dibenzoyloxy-2-cyclohexene and a Pd catalyzed cross-coupling constitute key reactions in a synthesis of the non-opioid analgesic (-)-epibatidine.