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(R)-3-Benzyl 4-Methyl 2,2-Dimethyloxazolidine-3,4-Dicarboxylate, with the molecular formula C18H21NO6, is a derivative of oxazolidine, a five-membered cyclic compound containing nitrogen, oxygen, and carbon atoms. This chiral molecule features a stereogenic center at the carbon bonded to the nitrogen atom in the oxazolidine ring. Its unique structure and chirality make it a valuable intermediate in organic synthesis, particularly for the production of pharmaceuticals and agrochemicals. Additionally, (R)-3-Benzyl 4-Methyl 2,2-Dimethyloxazolidine-3,4-Dicarboxylate exhibits potential biological and pharmacological activities, which contribute to its significance in the research and development of novel drugs.

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  • 133464-35-4 Structure
  • Basic information

    1. Product Name: (R)-3-BENZYL 4-METHYL 2,2-DIMETHYLOXAZOLIDINE-3,4-DICARBOXYLATE
    2. Synonyms: (R)-3-BENZYL 4-METHYL 2,2-DIMETHYLOXAZOLIDINE-3,4-DICARBOXYLATE
    3. CAS NO:133464-35-4
    4. Molecular Formula: C15H19NO5
    5. Molecular Weight: 293.32
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 133464-35-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: (R)-3-BENZYL 4-METHYL 2,2-DIMETHYLOXAZOLIDINE-3,4-DICARBOXYLATE(CAS DataBase Reference)
    10. NIST Chemistry Reference: (R)-3-BENZYL 4-METHYL 2,2-DIMETHYLOXAZOLIDINE-3,4-DICARBOXYLATE(133464-35-4)
    11. EPA Substance Registry System: (R)-3-BENZYL 4-METHYL 2,2-DIMETHYLOXAZOLIDINE-3,4-DICARBOXYLATE(133464-35-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 133464-35-4(Hazardous Substances Data)

133464-35-4 Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-Benzyl 4-Methyl 2,2-Dimethyloxazolidine-3,4-Dicarboxylate is used as an intermediate in the synthesis of various pharmaceutical compounds due to its chiral nature and unique structural features. Its ability to be incorporated into complex molecular structures makes it a valuable building block for the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical industry, (R)-3-Benzyl 4-Methyl 2,2-Dimethyloxazolidine-3,4-Dicarboxylate is utilized as a key intermediate in the synthesis of chiral agrochemicals. Its incorporation into these compounds can lead to enhanced target specificity, reduced environmental impact, and improved overall performance.
Used in Research and Development:
(R)-3-Benzyl 4-Methyl 2,2-Dimethyloxazolidine-3,4-Dicarboxylate is also used in the research and development of new drugs, particularly those with potential biological and pharmacological activities. Its unique structure and chirality make it an attractive candidate for exploring novel therapeutic approaches and advancing the understanding of molecular interactions in various biological systems.

Check Digit Verification of cas no

The CAS Registry Mumber 133464-35-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,3,4,6 and 4 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 133464-35:
(8*1)+(7*3)+(6*3)+(5*4)+(4*6)+(3*4)+(2*3)+(1*5)=114
114 % 10 = 4
So 133464-35-4 is a valid CAS Registry Number.

133464-35-4Relevant articles and documents

HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF ABNORMAL CELLULAR PROLIFERATION

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Page/Page column 127-128, (2019/07/20)

This invention is in the area of heterocyclic-based compounds for the treatment of disorders involving abnormal cellular proliferation, including but not limited to tumors and cancers.

DIPEPTIDE AND TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS

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, (2014/10/04)

Provided herein are dipeptide and tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of proliferative diseases including cancer and autoimmune diseases.

Development of a scalable chiral synthesis of MK-3281, an inhibitor of the hepatitis C virus NS5B polymerase

Colarusso, Stefania,Conte, Immacolata,Di Filippo, Marcello,Ercolani, Caterina,MacKay, Angela C.,Palumbi, Maria Cecilia,Rico Ferreira, Maria Del Rosario,Stansfield, Ian,Zaramella, Simone,Narjes, Frank,Habermann, J?rg

scheme or table, p. 1527 - 1532 (2011/08/03)

The development of a scalable chiral synthesis for the HCV NS5B inhibitor MK-3281 is being reported. Several alternative routes were explored and are being described. Georg Thieme Verlag Stuttgart ? New York.

4,4-Difluorinated analogues of l-arginine and NG-hydroxy-l-arginine as mechanistic probes for nitric oxide synthase

Martin, Nathaniel I.,Woodward, Joshua J.,Winter, Michael B.,Marletta, Michael A.

supporting information; experimental part, p. 1758 - 1762 (2009/11/30)

4,4-Difluoro-l-arginine and 4,4-difluoro-NG-hydroxy-l-arginine were synthesized and shown to be substrates for the inducible isoform of nitric oxide synthase (iNOS). Binding of both fluorinated analogues to the NOS active site was also investigated using a spectral binding assay employing a heme domain construct of the inducible NOS isoform (iNOSheme). 4,4-Difluoro-NG-hydroxy-arginine was found to bind at the NOS active site in a unique manner consistent with a model involving ligation of the FeIII heme center by the oxygen atom of the NG-hydroxy moiety.

Rearrangement of N-alkyl 1,2-amino alcohols. Synthesis of (S)-toliprolol and (S)-propanolol

Duthion, Béranger,Métro, Thomas-Xavier,Gomez Pardo, Domingo,Cossy, Janine

experimental part, p. 6696 - 6706 (2011/02/26)

N-alkyl 1,2-amino alcohols were rearranged stereospecifically by using TFAA/Et3N. This rearrangement has been used to synthesize N-isopropyl-3-(aryloxy)-2-hydroxypropylamines, β-adrenergic blocking agents such as (S)-toliprolol and (S)-propanolol.

The synthesis of (2S)-4,4-difluoroglutamyl γ-peptides based on Garner's aldehyde and fluoro-reformatsky chemistry

Konas, David W.,Pankuch, Jessica J.,Coward, James K.

, p. 2616 - 2626 (2007/10/03)

The development of optically active fluorinated synthetic building blocks of general utility is a current goal of organo-fluorine chemists. The serine-derived Garner aldehyde was converted to a general 4,4-difluoroamino acid building block via fluoro-Reformatsky reaction with ethyl bromodifluoroacetate. The utility of this building block was demonstrated by the synthesis of derivatives of (2S)-4,4-difluoroglutamine, (2S)-4,4-difluoroglutamic acid, and its incorporation into a fluorophore-containing isopeptide 2 designed as a mechanistic probe of γ-glutamyl hydrolase. Compound 2 proved to be a substrate for γ-glutamyl hydrolase and was hydrolyzed at a rate significantly slower than the corresponding non-fluorinated analog.

First stereocontrolled synthesis of (S)-cleonin and related cyclopropyl-substituted amino acids.

Esposito,Piras,Ramazzotti,Taddei

, p. 3273 - 3275 (2007/10/03)

[reaction: see text]. Enantiomerically pure (S)-cleonin, a key component of the antitumor antibiotic cleomycin, was prepared starting from (R)-serine. The Kulinkovich cyclopropanation of the methyl ester of N-Cbz serine acetonide gave the hydroxycyclopropyl moiety. The amino alcohol region was further oxidized to amino acid. The Kulinkovich cyclopropanation allowed also the preparation of other non-natural substituted cyclopropylglycines.

The synthesis of substituted (4S)-4-(hydroxymethyl)imidazolidin-2-ones as novel protein kinase C modulators

Zhao,Qiao,Rong,Kozikowski

, p. 8711 - 8715 (2007/10/03)

The total synthesis of substituted (4S)-4-(hydroxymethyl)imidazolidin-2-ones from D-serine methyl ester is described. The key step in the synthesis is a reductive amination reaction which is brought about using titanium(IV) isopropoxide and sodium cyanoborohydride, followed by the cyclization to urea using triphosgene after deprotection. (C) 2000 Elsevier Science Ltd.

Enantiospecific synthesis of (R)- and (S)-2,3-diaminopropanol from L- and D-serine

Demirci, Fatih,Haines, Alan H.,Jia, Chunhua,Wu, Di

, p. 189 - 191 (2007/10/03)

Both chiral forms of 2,3-diaminopropanol (6) have been prepared in a convenient 5-step synthesis based on the readily available N-benzyloxycarbonyl derivatives of the methyl esters of L- and D-serine.

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