141807-59-2

Usage

Uses

Used in Pharmaceutical Industry:
8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 8-methyl-3-(4-methylphenyl)-, (1R,2S,3S,5S)is used as a building block or intermediate in the synthesis of biologically active compounds for pharmaceutical applications. Its unique structure and functional groups may contribute to the development of new drugs with specific therapeutic effects.
Used in Research and Development:
8-Azabicyclo[3.2.1]octane-2-carboxylic acid,
8-methyl-3-(4-methylphenyl)-, (1R,2S,3S,5S)is utilized in research and development for understanding its properties, reactivity, and potential interactions with biological systems. Its chirality and structural features make it an interesting subject for studying the relationship between molecular structure and biological activity.
Used in Drug Design and Optimization:
8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 8-methyl-3-(4-methylphenyl)-, (1R,2S,3S,5S)can be used as a starting point or a key component in the design and optimization of new drugs. Its structural features may be incorporated into drug candidates to improve their pharmacokinetic and pharmacodynamic properties, leading to more effective and safer medications.
Used in Chiral Chemistry:
The chirality of 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 8-methyl-3-(4-methylphenyl)-, (1R,2S,3S,5S)- makes it a valuable tool in chiral chemistry, where the stereochemistry of molecules plays a crucial role in their biological activity and selectivity. It can be used to study the effects of stereochemistry on drug-receptor interactions and to develop enantioselective synthetic methods for the production of chiral drugs.

Upstream product

• 50-00-0 formaldehyd 
• 56-41-7 L-alanin 
• 96293-17-3 (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide 
• 117176-06-4 (S)-4-Methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 121704-29-8 3-Hydroxy-2-(2-methoxy-acetylamino)-2-methyl-propionic acid 
• 114396-62-2 (S)-α-methylserine hydrochloride 
• 1059607-23-6 (1S,4S,7S,8R)-4,8,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one 
• 1059607-17-8 (1R,4S,7R,8S)-1,4,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one 
• 83537-82-0 methyl (2R)-2-amino-3-(benzyloxy)-2-methylpropanoate 
• 134899-85-7 α-methyl serine hydrochloride 
• 1059607-24-7 (1S,4R,7S,8R)-4,8,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one 
• 1059607-25-8 (1R,4R,7R,8S)-1,4,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one 
• 130342-81-3 RTI-32 
• 4294-57-9 para-methylphenylmagnesium bromide 

Downstream Products

• 398497-73-9 (1R,2S,3S,5S)-8-Methyl-3-p-tolyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 3-methanesulfonyloxy-propyl ester 
• 204071-17-0 (1R,2S,3S,5S)-8-Methyl-3-p-tolyl-8-aza-bicyclo[3.2.1]octane-2-carbonyl chloride 
• 146145-20-2 3β-(4'-methylphenyl)tropane-2β-carboxylic acid phenyl ester 
• 146145-19-9 3β-(4'-methylphenyl)tropan-2β-carboxylic acid isopropyl ester 
• 176698-62-7 Benzoic acid N'-((1R,2S,3S,5S)-8-methyl-3-p-tolyl-8-aza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazide 
• 947595-22-4 3β-(4-methylphenyl)tropane-2β-N-3,4-dimethoxyphenacylcarboxthioamide ethylene ketal 
• 947595-18-8 3β-(4-methylphenyl)tropane-2β-N-(3,4-dichlorophenacyl)carboxthioamide ethylene ketal 
• 947594-98-1 C₂₄H₂₇BrN₂O₂ 
• 947595-21-3 3β-(4-methylphenyl)tropane-2β-N-3,4-dimethoxyphenacylcarboxamide ethylene ketal 
• 947595-17-7 3β-(4-methylphenyl)tropane-2β-N-(3,4-dichlorophenacyl)carboxamide ethylene ketal 
• 947595-09-7 3β-(4-methylphenyl)tropane-2β-N-3-nitrophenacylcarboxamide ethylene ketal 

Relevant academic research and scientific papers

Enzyme-Catalysed Hydrolysis of Some Functionalized Dimethyl Malonates

A method is described for the preparation of (+)-(R)-methyl hydrogen 2-(tert-butoxymethyl)-2-methylmalonate (5e) in synthetically useful amounts from readily available starting material.

PREPARATIVE ASYMMETRIC SYNTHESIS OF (R)- AND (S)-α-METHYLSERINE Ni(II) COMPLEX WITH A SCHIFF BASE OF α-ALANINE AND (S)-2-BENZOPHENONE

The kinetic and thermodynamic diastereoselectivity of the hydroxymethylation of the alanine fragment in the Ni(II) complex of the Schiff base of alanine and (S)-2-benzophenone (BBP) was studied.Optically pure (R)- and (S)-α-methylserines were synthesized.

A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones

An efficient synthesis of (+)-conagenin, a novel immunomodulator produced by Streptomyces roseosporus, has been achieved via the shortest route at present. At the same time, 2-epiconagenin was synthesized according to the same methodology.

Cloning of the gene encoding α-methylserine hydroxymethyltransferase from Aminobacter sp. AJ110403 and Ensifer sp. AJ110404 and characterization of the recombinant enzyme

Genes encoding α-methylserine hydroxymethyltransferase from Aminobacter sp. AJ110403 and Ensifer sp. AJ110404 were cloned and expressed in Escherichia coli. The purified enzymes were homodimers with a 46-kDa subunit and contained 1 mol/mol-subunit of pyridoxal 5′-phosphate. The V max of these enzymes catalyzing the conversion of α-methyl-L-serine to D-alanine via tetrahydrofolate was 22.1 U/mg (AJ110403) and 15.4 U/mg (AJ110404).

Asymmetric synthesis of (S)-and (R)-α-methylserine based on the chiral recyclable reagent (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

Both enantiomers of α-methylserine were synthesized with the use of NiII complexes based on the chiral recyclable reagent (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide. Intermediate diastereomeric complexes were separated by crystal

Method for preparing 2-methylserine

The invention relates to a method for preparing 2-methylserine, and mainly solves the technical problem of being long in route, complicated in operation, and not conducive to mass production of the existing synthetic method. The method comprises the following steps: Cbz-chiral alanine and Benzaldehyde dimethyl acetal are reacted under the action of thionyl chloride and zinc chloride, a reaction product is crystallized to obtain an intermediate 1, the intermediate 1 is reacted under cooperation of an alkaline reagent to obtain an intermediate 2, an intermediate 3 is obtained from the intermediate 2 by the action of lithium hydroxide, and the final product 2-methylserine is obtained from the intermediate 3 by palladium carbon catalytic hydrogenolysis. High purity 2-methylserine can be obtained by the method.

Theoretical evidence for pyramidalized bicyclic serine enolates in highly diastereoselective alkylations

A new chiral serine equivalent and its enantiomer have been synthesized from (S)- and (R)-N-Bocserine methyl esters (Boc: tert-butyloxy-carbonyl). The use of these compounds as chiral building blocks has been demonstrated in the synthesis of α-alkyl α-amino acids by diastereoselective po tassium enolate alkylation reactions and subsequent acid hydrolyses. Theoretical studies were performed to eluci date the stereochemical outcome of both the formation of five-membered cyclic N,O-acetals and the subsequent alkylation process, which occurs with total retention of configuration. This feature could be explained in terms of the high degree of pyramidalization of enolate intermediates.

Stereoselective addition of organometallic reagents to a chiral acyclic nitrone derived from L-erythrulose

The additions of various organolithium and organomagnesium reagents to a chiral nitrone prepared from L-erythrulose took place with variable diastereoselectivity. The degree and strength of the facial selectivity can be modified if the reaction is performed in the presence of Lewis acid additives: zinc bromide enhances the attack to the Si face of the C=N bond whereas diethyl aluminium chloride promotes attack to the Re face. The obtained adducts can be then transformed into protected N-hydroxy-α,α-disubstituted-α- amino acid derivatives as well as into the corresponding α,α- disubstituted α-amino acids.

Enantioselective synthesis of α-methyl-D-cysteine and lanthionine building blocks via α-methyl-d-serine-β-lactone

(Matrix presented) We report here the enantioselective synthesis of Boc-α-methyl-D-cysteine(PMB)-OH and lanthionine building blocks through the regioselective ring opening of key intermediate Boc-α -methyl-D-serine-β-lactone.

Synthesis of α,α-disubstituted α-amino acid derivatives in enantiopure form via stereoselective addition of Grignard reagents to a chiral acyclic nitrone derived from L-erythrulose

The additions of various Grignard reagents to a chiral nitrone prepared from L-erythrulose take place with variable diastereoselectivity. The degree and strength of the facial selectivity can be modified if the reaction is performed in the presence of Lewis acidic additives: zinc bromide enhances attack to the si face whereas diethyl aluminum chloride promotes attack to the re side. The obtained adducts can be then efficiently transformed into protected N-hydroxy α,α-disubstituted α-amino acid derivatives as well as into the corresponding α,α-disubstituted α-amino acids.