118399-28-3

Basic information

• Product Name: Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate
• Synonyms: (R)-BENZYL-5-OXO-TETRAHYDROFURAN-3-YL CARBAMATE;BENZYL (R)-5-OXOTETRAHYDROFURAN-3-YLCARBAMATE;N-[(3R)-Tetrahydro-5-oxo-3-furanyl]carbamic acid phenylmethyl ester;3(R)-[(Carbobenzyloxy)amino]-γ-butyrolactone;Cbz-R-3-Amino-γ-butyrolactone;(R)-3-(Cbz-aMino)-5-oxotetrahydrofuran;(R)-4-benzyloxycarbonylaMino-4,5-dihydro-2(3H)-furanone 10g;(R)-4-(Cbz-aMino)-2-oxotetrahydrofuran
• CAS NO: 118399-28-3
• Molecular Formula: C₁₂H₁₃NO₄
• Molecular Weight: 235.23592
• EINECS: 821-246-2
• Product Categories: chiral;Chiral Reagents;Amino Acids & deravitives;Aromatics;Heterocycles;Miscellaneous Reagents
• Mol File: 118399-28-3.mol

Chemical Properties

• Melting Point: 105.0 to 109.0 °C
• Boiling Point: 466.087 °C at 760 mmHg
• Flash Point: 235.681 °C
• Appearance: Off-white solid
• Density: 1.27
• Vapor Pressure: 7.29E-09mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• PKA: 10.87±0.20(Predicted)
• CAS DataBase Reference: Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate(118399-28-3)
• EPA Substance Registry System: Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate(118399-28-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 118399-28-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate is used as a synthetic intermediate for the development of various organic compounds. Its carbamate functional group allows for further chemical reactions and modifications, making it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate is used as a key component in the synthesis of drugs targeting specific medical conditions. Its unique structure and reactivity enable the development of novel therapeutic agents with improved efficacy and selectivity.
Used in Agrochemical Industry:
Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate is also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its incorporation into these products can lead to enhanced performance and selectivity, ultimately contributing to more effective and environmentally friendly agricultural practices.

InChI:InChI=1/C12H13NO4/c14-11-6-10(8-16-11)13-12(15)17-7-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,13,15)/t10-/m1/s1

Upstream product

• 75443-62-8 benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate 
• 123673-31-4 (R)-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid 
• 105183-60-6 (S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate 
• 1783-96-6 (2R)-aspartic acid 
• 501-53-1 benzyl chloroformate 
• 135517-09-8 ((1S,2R)-3-Benzylcarbamoyl-2-benzyloxycarbonylamino-1-hydroxymethyl-propyl)-carbamic acid tert-butyl ester 
• 1256257-81-4 C₁₄H₁₃F₃N₂O₅ 
• 130369-36-7 N-(Benzyloxycarbonyl)-3-amino-1-cyclobutanone 
• 30925-18-9 2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester 
• 78663-07-7 N-(benzyloxycarbonyl)-D-aspartic acid 

Downstream Products

• 126456-05-1 ((3R,4S)-4-Methyl-5-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester 
• 126456-07-3 Benzyl [(3R,4R)-4-methyl-5-oxo-tetrahydrofuran-3-yl]-carbamate 
• 349148-56-7 (3R,4R)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone 
• 152580-30-8 (R)-β-amino-γ-butyrolactone 
• 349148-60-3 (2R,3R)-N-methoxy-N-methyl-2-benzyl-3,4-(benzyloxycarbonylimino)-butanamide 
• 349148-58-9 (2R,3R)-N-methoxy-N-methyl-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanamide 
• 870812-92-3 benzyl (1R)-1-(hydroxymethyl)-3-(4-morpholinyl)-3-oxopropylcarbamate 
• 870812-29-6 benzyl (1R)-3-(dimethylamino)-1-(hydroxymethyl)-3-oxopropylcarbamate 
• 896123-15-2 benzyl (2-hydroxy-(1R)-1-{[2-fluoro-4-(3-oxomorpholin-4-yl)phenylcarbamoyl]methyl}ethyl)carbamate 
• 152783-42-1 (R)-4-benzylamino-4,5-dihydro-2(3H)-furanone 
• 870812-30-9 benzyl {(1R)-3-(dimethylamino)-3-oxo-1-[(phenylthio)methyl]propyl}carbamate 
• 1012059-95-8 (R)-benzyl 1-hydroxy-4-(methylamino)-4-oxobutan-2-ylcarbamate 
• 921751-96-4 C₂₄H₂₆F₃N₃O₅ 
• 921752-04-7 benzyl [(3R,4R)-4-allyl-5-oxotetrahydrofuran-3-yl]carbamate 

Relevant articles and documents

INHIBITING B-CELL LYMPHOMA 2 (BCL-2) AND RELATED PROTEINS

Novel compounds inhibiting anti-apoptosis proteins B-cell lymphoma 2 (Bcl-2) and Bcl-XL include compounds of formula (I) and formula (II) disclosed herein, as well as liposome compositions comprising Bcl-2 inhibitor compounds. These compositions are usefu

Baeyer–Villiger monooxygenase-catalyzed desymmetrizations of cyclobutanones. Application to the synthesis of valuable spirolactones

A series of γ-butyrolactone derivatives, including some spiranic ones, was obtained through desymmetrization of the corresponding prochiral 3-substituted cyclobutanones via Baeyer–Villiger monooxygenase (BVMO)-catalyzed oxidation. After reaction optimization using several commercial enzymes, both antipodes of various lactones were synthesized in most cases with >90% conversion and >80% enantiomeric excess under mild reaction conditions. In some cases alcohol formation was also observed (up to 40% conversion) as an undesired side reaction due to the presence of alcohol dehydrogenases in these preparations. Selected transformations were achieved on a 100 mg scale showing the possibilities of these oxidative biocatalysts as a new source of highly interesting compounds.

CHEMICAL COMPOUNDS

The present invention relates to compounds of Formula (I): and to their salts, pharmaceutical compositions, methods of use, and methods for their preparation. These compounds inhibit Bcl-2 and/or Bcl-XL activities and may be used for the treatment of cancer.

Highly efficient and practical pyrrolidine-camphor-derived organocatalysts for the direct α-amination of aldehydes

A series of pyrrolidine-camphor-derived organocatalysts (1-4) were designed and synthesised. These organocatalysts were used for direct α-amination of aldehydes with dialkyl azodicarboxylates to give the desired α-aminated products in high chemical yields

Design and synthesis of some new quinoline-3-carbohydrazone derivatives as potential antimycobacterial agents

A series of 26 new quinoline derivatives carrying active pharmacophores has been synthesized and evaluated for their in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv (MTB), Mycobacterium smegmatis (MC2), and Mycobacterium fortuitum following the broth micro dilution assay method. Compounds 13e, 13i, 13k, 14a, 14c, 14i, and 14k exhibited significant minimum inhibition concentrations, when compared with first line drugs isoniazid (INH) and rifampicin (RIF) and could be ideally suited for further modifications to obtain more efficacious compounds in the fight against multi-drug resistant tuberculosis.

BCL-2 INHIBITORS CONTAINING A ZINC BINDING MOIETY

The present invention relates to Bcl-2 inhibitors and their use in the treatment of cell proliferative diseases such as cancer. The compounds of the invention may further act as HDAC inhibitors

ARYLSULFONAMIDE COMPOUNDS

The invention relates generally to small molecules that mimic the biological activity of certain peptides and proteins, to compositions containing them and to their use. In particular, the invention relates to compounds of the general formula (I) that mim

N-sulfonylcarboximidamide apoptosis promoters

Compounds having the formula are apoptosis promoters. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

N substituted 3-amino-2,2-di-c-alkyl-1,4-butyrolactones and 1,4-thiobutyrolactones for use as promoter of γ-aminobutyric acid activity and for treating nervous disorders and preparation method

The invention concerns compounds represented by general formula (I) wherein: Z represents a sulfur or oxygen atom; the groups R1 and R2, identical or different, represent each a alkyl group or an alkenyl group; X represents a CO, a CO2, an SO, or an SO2and the group R represents an alkyl, aryl, alkenyl, or aralkyl group, provided that when Z represents an oxygen atom, X an SO2and R a group (a), R1 and R2 do not both represent the methyl group. The invention also concerns methods for preparing said compounds, pharmaceutical compositions containing them and their use as promoter of γ-aminobutyric acid and as medicine particularly designed for treating nervous disorders.

New nodularins: A general method for structure assignment

A general method has been developed for assigning the structures of nodularin, a potent hepatotoxin, tumor promoter, and protein phosphatase inhibitor, and minor components isolated from a cultured and a bloom sample of the cyanobacterium Nodularia spumigena. It consists of (1) FABMS analysis (determination of molecular weight and molecular formula), (2) 1H NMR spectroscopy on the parent compound and chiral GC analysis of an acid hydrolyzate (identification and stereochemistry of amino acid components), (3) ozonolysis followed by NaBH4 reduction (conversion to a linear peptide), and (4) FABMS/CID/MS analyses of the linear peptide and the parent compound (sequence analysis). The method has been employed in assigning structures to three new nodularins (2-4) and can be applied to other cyclic peptides containing α,β-dehydroamino acid unit(s), especially the related microcystins, cyclic heptapeptide hepatotoxins. Two nodularins, [DMAdda3]nodularin (2) and [(6Z)Adda3]nodularin (3), were obtained from a bloom sample collected from Lake Ellesmere (New Zealand), and [D-Asp1]nodularin (4) was isolated from cultured cells (strain L-575). The LD50s of 2 and 4 were 150 and 75 μg/kg (ip, mice), respectively, but 3 did not show apparent toxicity at 2.0 mg/kg.