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(1R,2R,5S)-rel-3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid is a bicyclic compound that is a derivative of azabicyclo[3.1.0]hexane, featuring a tert-butoxycarbonyl group attached to the nitrogen atom. (1R,2R,5S)-rel-3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid is recognized for its unique structure and stereochemistry, which render it a valuable asset in the field of organic synthesis.

72448-25-0

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  • (1R,2R,5S)-rel-3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

    Cas No: 72448-25-0

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72448-25-0 Usage

Uses

Used in Pharmaceutical Synthesis:
(1R,2R,5S)-rel-3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid serves as a chiral building block in the preparation of various pharmaceuticals. Its distinctive stereochemistry allows for the creation of enantiomerically pure compounds, which is crucial for the development of drugs with specific biological activities and reduced side effects.
Used in Organic Synthesis:
In the realm of organic synthesis, (1R,2R,5S)-rel-3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid is utilized for the introduction of specific functional groups and stereochemical elements into organic molecules. Its versatility in asymmetric synthesis makes it an indispensable tool for chemists aiming to construct complex molecular architectures with high selectivity.
Used in Biologically Active Molecule Preparation:
(1R,2R,5S)-rel-3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid is also employed in the synthesis of biologically active molecules, where its unique structural features contribute to the development of molecules with potential applications in medicine, agriculture, and other fields. The ability to manipulate its structure for specific interactions with biological targets underscores its importance in this area.
Used in Asymmetric Synthesis:
(1R,2R,5S)-rel-3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid is particularly valuable in asymmetric synthesis, where the need for enantioselective reactions is paramount. Its predictable and controllable stereochemistry facilitates the synthesis of compounds with a single enantiomer, which is essential for avoiding potential adverse effects associated with the presence of unwanted enantiomers in pharmaceuticals and other applications.

Check Digit Verification of cas no

The CAS Registry Mumber 72448-25-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,2,4,4 and 8 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 72448-25:
(7*7)+(6*2)+(5*4)+(4*4)+(3*8)+(2*2)+(1*5)=130
130 % 10 = 0
So 72448-25-0 is a valid CAS Registry Number.

72448-25-0Downstream Products

72448-25-0Relevant articles and documents

IMMUNOPROTEASOME INHIBITORS

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, (2018/08/20)

Provided herein are compounds, such as a compound of Formula (I), as described herein, or a pharmaceutically acceptable salt thereof, that are immunoproteasome (such as LMP2 and LMP7) inhibitors. The compounds described herein can be useful for the treatment of diseases treatable by inhibition of immunoproteasomes. Also provided herein are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

ARYL, HETEROARYL, AND HETEROCYCLIC COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

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, (2017/03/14)

Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is an aryl, heteroaryl or heterocycle (R32) are provided. The inhibitors of Factor D described herein reduce the excessive activation of complement.

1-(HET)ARYLSULFONYL-(PYRROLIDINE OR PIPERIDINE)-2-CARBOXAMIDE DERIVATIVES AND THEIR USE AS TRPA1 ANTAGONISTS

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, (2016/09/22)

The invention is concerned with the compounds of formula I and salts thereof and other compounds of formulas II-IX as disclosed herein. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formulas I-IX as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain or asthma.

COMBINATIONS OF HEPATITIS C VIRUS INHIBITORS

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Page/Page column 602, (2015/02/02)

The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

Synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3- azabicyclo[3.1.0]hexane-2-carboxylic acid

Bakonyi, Bettina,Furegati, Markus,Kramer, Christian,La Vecchia, Luigi,Ossola, Flavio

, p. 9328 - 9339 (2013/10/08)

A synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3- azabicyclo[3.1.0]hexane-2-carboxylic acid has been developed, thereby significantly shortening the known literature procedures for the syntheses of these unnatural amino acids. With a simple adjustment of the reaction conditions, we were able to obtain either pure cis or trans acid. Optical resolution was accomplished via diastereomeric salt formation or alternatively via chromatography on a chiral stationary phase. Finally, ab initio calculations gave an explanation for the observed cis selectivity in the initial step.

Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II

Yu, Li-Fang,Eaton, J. Brek,Fedolak, Allison,Zhang, Han-Kun,Hanania, Taleen,Brunner, Dani,Lukas, Ronald J.,Kozikowski, Alan P.

, p. 9998 - 10009 (2013/01/16)

In our continued efforts to develop α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists as novel antidepressants having a unique mechanism of action, structure-activity relationship (SAR) exploration of certain isoxazolylpyridine ethers is presented. In particular, modifications to both the azetidine ring present in the starting structure 4 and its metabolically liable hydroxyl side chain substituent have been explored to improve compound druggability. The pharmacological characterization of all new compounds has been carried out using [3H]epibatidine binding studies together with functional assays based on 86Rb+ ion flux measurements. We found that the deletion of the metabolically liable hydroxyl group or its replacement by a fluoromethyl group not only maintained potency and selectivity but also resulted in compounds showing antidepressant-like properties in the mouse forced swim test. These isoxazolylpyridine ethers appear to represent promising lead candidates in the design of innovative chemical tools containing reporter groups for imaging purposes and of possible therapeutics.

3-AZA-BICYCLO[3.1.0]HEXANE DERIVATIVES

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Page/Page column 48, (2010/02/17)

The invention relates to 3-aza-bicyclo[3.1.0]hexane derivatives of formula (I) wherein A, B, n, X, and R1 are as described in the description, and salts thereof, and their use as orexin receptor antagonists.

3-AZA-BICYCLO[3.1.0]HEXANE DERIVATIVES

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Page/Page column 94-95, (2008/06/13)

The invention relates to 3-aza-bicyclo[3.1.0]hexane derivatives of formula (I) wherein A, B, n, X, and R1 are as described in the description, and salts thereof, and their use as orexin receptor antagonists.

MACROCYCLIC COMPOUNDS AS HCV NS3 PROTEASE INHIBITORS

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Page/Page column 248-249, (2008/12/08)

The present application describes macrocyclic compounds of formula (I) with NS3 protease inhibitory activity for treating hepatitis C virus infection.

Non-covalent inhibitors of urokinase and blood vessel formation

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, (2008/06/13)

Novel compounds having activity as non-covalent inhibitors of urokinase and having activity in reducing or inhibiting blood vessel formation are provided. These compounds have P1 a group having an amidino or guanidino moiety or derivative thereof. These compounds are useful in vitro for monitoring plasminogen activator levels and in vivo in treatment of conditions which are ameliorated by inhibition of or decreased activity of urokinase and in treating pathologic conditions wherein blood vessel formation is related to a pathologic condition.

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