20585-32-4

Upstream product

• 165879-50-5 (+)-(benzoyl)-2 phenyl-3 diazabicyclo-1,3 <3,3,O> octane 
• 931-50-0 cyclohexylmagnesium bromide 
• 135033-59-9 (S)-Cyclohexyl-phenyl-(3R,7aS)-tetrahydro-pyrrolo[1,2-c]oxazol-3-yl-methanol 
• 20585-31-3 (1S)-1-C-Cyclohexyl-1-C-phenyl-D-arabinit 
• 913370-10-2 (S)-Benzyloxy-cyclohexyl-phenyl-acetaldehyde 
• 1259391-28-0 (Z)-3-(2-phenyl-2-cyclohexyl)oxazolidin-2-one 
• 135033-55-5 (2R)-Benzoyl-3-oxa-1-azabicyclo<3.3.0>octane 
• 10074-42-7 cyclohexyllithium 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 1074-12-0 phenylglyoxal hydrate 
• 503183-77-5 (S)-cyclohexyl(phenyl)[(trimethylsilyl)oxy]acetonitrile 
• 712-50-5 Cyclohexyl phenyl ketone 
• 913370-05-5 (2R)-1,2-O-cyclohexylidene-3-phenylpropane-3-ol 
• 654077-26-6 (2R)-1,2-O-cyclohexylidene-3-phenylpropan-3-one 

Downstream Products

• 20585-33-5 S-(+)-phenyl-2 cyclohexyl-2 hydroxy-2 acetate de methyle 
• 20585-34-6 (S)-cyclohexylmandelic acid 
• 102473-43-8 Toluene-4-sulfonic acid (S)-3-cyclohexyl-3-hydroxy-3-phenyl-propyl ester 
• 114499-81-9 (S)-(+)-1-cyclohexyl-1-phenyl-1,3-propanediol 
• 135033-61-3 (S)-(+)-1-cyclohexyl-1-phenyl-2-propen-1-ol 
• 40520-24-9 (+)-Trihexyphenidyl 
• 91704-75-5 (S)-(-)-1-cyclohexyl-1-phenyl-1,2-etanediol 
• 201942-95-2 (-)-2-cyclohexyl-N-(4-dimethylamino-2-butynyl)-2-hydroxy-2-phenylacetamide 

Relevant academic research and scientific papers

A practical synthesis of (S)-oxybutynin

(S)-Oxybutynin, an important drug acting as muscarinic receptor antagonist, was practically synthesized using catalytic enantioselective cyanosilylation of cyclohexyl phenyl ketone (6a) as a key step. Cyanohydrin 7a with 94% ee was obtained with 1 mol% of

Catalytic asymmetric dihydroxylation of enamides and application to the total synthesis of (+)-tanikolide

Asymmetric dihydroxylation of β,β- disubstituted enamides afforded chiral tertiary-alcohol-containing α-hydroxyaldehydes and 1,2-diols with high enantioselectivity (see scheme). This method was applied to the total synthesis of the antifungal natural prod

Enantioselective synthesis of α-tertiary hydroxyaldehydes by palladium-catalyzed asymmetric allylic alkylation of enolates

Chiral α-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available α-halo or α-hydroxy ketones or enol silyl ethers with excellent yields and enantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity. Copyright

An efficient asymmetric synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid, the acid segment of oxybutynin

An innovative and facile synthesis of the title compound has been developed starting from (R)-cyclohexylidene glyceraldehyde. The key step in the synthesis is a chiral template-driven Grignard addition with absolute diastereocontrol. The other attractive features are the operational simplicity and the use of inexpensive compounds/reagents.

Catalytic asymmetric synthesis of (S)-oxybutynin and a versatile intermediate for antimuscarinic agents

A practical synthesis of (S)-oxybutynin, a muscarinic receptor antagonist, using catalytic enantioselective cyanosilylation of cyclohexyl phenyl ketone (9a) as a key step is described. The key reaction proceeded with 94% ee using 1 mol% of Gd-1 catalyst,

Agents for the treatment of overactive detrusor. III. Synthesis and structure-activity relationships of N-(4-amino-2-butynyl)acetamide derivatives

A series of N-(4-amino-2-butynyl)acetamides were synthesized and examined for their inhibitory activity on detrusor contraction and mydriatic activity as an index of anticholinergic side effect. Among those compounds synthesized, (+)-2-cyclohexyl-N-(4-dimethylamino-2-butynyl)-2-hydroxy-2-phenylaceta mide hydrochloride ((+)-13b·HCl), 2-cyclohexyl-2-hydroxy-N-(4-methylamino-2-butynyl)-2-phenylacetamide hydrochloride (13c·HCl), N-(4-dimethylamino-2-butynyl)-2,2-diphenyl-2-hydroxyacetamide hydrochloride (14·HCl), and 2,2-diphenyl-N-(4-ethylamino-2-butynyl)-2-hydroxyacetamide hydrochloride (14b·HCl) showed equipotent inhibitory activity on detrusor contraction to oxybutynin (1) and less mydriatic activity. Further evaluation of these compounds as an agent for the treatment of overactive detrusor has been examined.

Stereodivergent synthesis of optically active tertiary alcohols via addition reaction of chiral 2-acyl oxazolidine with organometallics

It was observed that diastereoselectivity in an addition reaction to chiral 2-acyl oxazolidine, derived from (S)-prolinol, can be fully regulated under appropriate conditions. Addition of organotitanium triisopropoxides provided (S)-tertiary alcohols, while organolithium reagents afforded the corresponding (R)-alcohols. Application of this methodology was demonstrated in the synthesis of (+)- and (-)-trihexyphenidyl.

Dedoublement et determination de la configuration absolue des enantiomeres de l'acide (thienyl-3)-2 cyclohexyl-2 hydroxy-2 acetique. Application a la synthese d'esters anticholinergiques du quinuclidinol-3

Enantiomeric 2-(3-thienyl)-2-cyclohexyl-2-hydroxy acetic acids 1 were obtained by the resolution of (+/-)-1 using (+)- and (-)-ephedrine as the resolving agents, and by asymmetric synthesis; (+)-1 was assigned S absolute configuration (i) by comparing the circular dichroism spectra of a series of derivatives of 1 with those of the corresponding derivatives of S-(+)-2-phenyl-2-cyclohexyl-2-hydroxy acetic acid 1', and (ii) by application of the quasi-racemate method.On transesterification of the methyl esters of 1, R-(+)-2 and S-(-)-2, with R-(-)- or S-(+)-1-azabicyclo-3-octanol (or 3-quinuclidinol), the four diastereoisomers of 3-quinuclidinyl 2-(3-thienyl)-2-cyclohexyl-2-hydroxy-acetate were obtained, i.e., (+)-2R, 3'S-6, (-)-2S, 3'R-6, (+)-2R, 3'R-7, and (-)-2S, 3'S-7.These compounds exhibited anticholinergic activity.