82353-55-7

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-(1-METHYL-2-OXO-ETHYL)-CARBAMIC ACID BENZYL ESTER is used as an intermediate in the synthesis of N-protected α-amino aldehydes, which are essential components of peptide aldehydes with enzyme inhibitor activity. These inhibitors are vital for the development of drugs targeting specific enzymes involved in various diseases.
Used in Enzyme Inhibitor Development:
In the field of enzyme inhibitor development, (S)-(1-METHYL-2-OXO-ETHYL)-CARBAMIC ACID BENZYL ESTER is used as a key building block for the synthesis of Leupeptin, a well-known serine protease inhibitor. (S)-(1-METHYL-2-OXO-ETHYL)-CARBAMIC ACID BENZYL ESTER helps in the design and synthesis of new enzyme inhibitors with potential therapeutic applications.
Used in Amino Sugar Preparation:
(S)-(1-METHYL-2-OXO-ETHYL)-CARBAMIC ACID BENZYL ESTER is also used in the preparation of amino sugars, which are important components of various biologically active molecules, including antibiotics, antifungals, and antiviral agents. Amino sugars play a crucial role in the development of glycobiology and glycochemistry.
Used in Unusual Amino Acid Synthesis:
In the synthesis of unusual amino acids, (S)-(1-METHYL-2-OXO-ETHYL)-CARBAMIC ACID BENZYL ESTER serves as a valuable precursor. Unusual amino acids are essential for the development of novel peptides and proteins with unique properties and potential applications in various industries, including pharmaceuticals, agriculture, and materials science.

Upstream product

• 28819-05-8 (S)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 6429-44-3 (S)-(-)-N-(benzyloxycarbonyl)alaninol 
• 1142-20-7 N-Cbz-Ala 
• 201230-82-2 carbon monoxide 
• 84713-20-2 benzyl N-vinylcarbamate 
• 3401-36-3 (N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester 
• 62023-24-9 [(R)-2-(3,5-Dimethyl-pyrazol-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid benzyl ester 
• 152169-60-3 benzyl {(2R)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate 
• 28819-05-8 N-benzyloxycarbonyl-D-alanine methyl ester 
• 26607-51-2 N-benzyloxycarbonyl-D-alanine 
• 102988-93-2 C₁₆H₂₁NO₆ 
• 501-53-1 benzyl chloroformate 
• 65638-93-9 N-Carbobenzoxy-L-alanin-kohlensaeureaethylesteranhydrid 
• 99790-15-5 ((S)-2-Imidazol-1-yl-1-methyl-2-oxo-ethyl)-carbamic acid benzyl ester 

Downstream Products

• 119372-47-3 (S)-4-Benzyloxycarbonylamino-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester 
• 127041-68-3 (2S,3SR)-2-{[(benzyloxy)carbonyl]amino}hex-5-en-3-ol 
• 114744-90-0 ((S)-2-Hydroxy-1-methyl-butyl)-carbamic acid benzyl ester 
• 104863-92-5 ((S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-carbamic acid benzyl ester 
• 105499-10-3 (1(S)-methyl-2-oxo-ethyl)-carbamic acid benzyl ester 
• 143914-91-4 (E)-(S)-4-Benzyloxycarbonylamino-2-methyl-pent-2-enoic acid ethyl ester 
• 127041-69-4 benzyl (2S,3R)-3-hydroxyhex-5-en-2-ylcarbamate 
• 127041-68-3 ((1S,2S)-2-Hydroxy-1-methyl-pent-4-enyl)-carbamic acid benzyl ester 
• 111854-78-5 (Z)-(S)-4-Benzyloxycarbonylamino-pent-2-enoic acid methyl ester 
• 218774-06-2 [(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-but-3-enyl]-carbamic acid benzyl ester 
• 218774-04-0 [(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-but-3-enyl]-carbamic acid benzyl ester 
• 241149-73-5 (2'R,3'S)-methyl 2-[3-(benzyloxycarbonylamino)-2-hydroxybutyl]propenoate 
• 241149-72-4 (2'S,3'S)-methyl 2-[3-(benzyloxycarbonylamino)-2-hydroxybutyl]propenoate 

Relevant academic research and scientific papers

Probing α-Amino Aldehydes as Weakly Acidic Pronucleophiles: Direct Access to Quaternary α-Amino Aldehydes by an Enantioselective Michael Addition Catalyzed by Br?nsted Bases

The high tendency of α-amino aldehydes to undergo 1,2-additions and their relatively low stability under basic conditions have largely prevented their use as pronucleophiles in the realm of asymmetric catalysis, particularly for the production of quaternary α-amino aldehydes. Herein, it is demonstrated that the chemistry of α-amino aldehydes may be expanded beyond these limits by documenting the first direct α-alkylation of α-branched α-amino aldehydes with nitroolefins. The reaction produces densely functionalized products bearing up to two, quaternary and tertiary, vicinal stereocenters with high diastereo- and enantioselectivity. DFT modeling leads to the proposal that intramolecular hydrogen bonding between the NH group and the carbonyl oxygen atom in the starting α-amino aldehyde is key for reaction stereocontrol.

Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis

Allylamines are versatile building blocks in the synthesis of various naturally occurring products and pharmaceuticals. In contrast to terminal allylamines, the methods of synthesis of their branched congeners with internal, stereodefined double bonds are less explored. This work describes a new approach for the preparation of allylaminesviacross-coupling of alkyl bromides with simple 3-bromoallylamines by merging the photoredox approach and Ni catalysis. The reaction proceeds under mild conditions, under blue light irradiation, and in the presence of an organic dye, 4CzIPN, as a photocatalyst. The scope of suitable reaction partners is broad, including alkyl bromides bearing reactive functionalities (e.g., esters, nitriles, aldehydes, ketones, epoxides) andN-protected allylamines, as well asN-allylated secondary and tertiary amines and heterocycles. The employment of non-racemic starting materials allows for rapid and easy construction of complex multifunctional allylamine derivatives without the loss of enantiomeric purity.

CHEMICAL COMPOUNDS

A compound of formula (I), wherein Ar1, R21, R23, R24, R25, R26, R27, A, X, Y and W are as defined herein. The compounds of the present invention are inhibitors of hematopoietic prostaglandin D synthase (H-PGDS) and can be useful in the treatment of Duchenne muscular dystrophy. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting H-PGDS activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

DIHYDROOROTATE DEHYDROGENASE INHIBITORS

Disclosed are compounds, compositions and methods for treating diseases, disorders, or medical conditions that are affected by the modulation of DHODH. Embodiments of such compounds are represented by Formula (I) as follows: 5 wherein R1, R2, R3, R4, R5a, R5b, X and Y, are defined herein.

Aldolase-Catalyzed Asymmetric Synthesis of N-Heterocycles by Addition of Simple Aliphatic Nucleophiles to Aminoaldehydes

Nitrogen heterocycles are structural motifs found in many bioactive natural products and of utmost importance in pharmaceutical drug development. In this work, a stereoselective synthesis of functionalized N-heterocycles was accomplished in two steps, com

Synthesis of chiral nine and twelve-membered cyclic polyamines from natural building blocks

A rational strategy for the facile and efficient cyclization of amino acid-based linear precursors forming nine and twelve-membered cyclic peptidomimetics is reported. The resulting chiral lactams can readily be reduced to substituted cyclic polyamine ana

Stereoselective addition of Grignard reagents to sulfinimines derived from tartrate diol (threitol): Generation of chiral building blocks for the collective total synthesis of lentiginosine, conhydrine and methyldihydropalustramate

A systematic investigation of the addition of Grignard reagents to sulfinimines derived from tartaric acid diol was undertaken. It was observed that the chirality of the inherent tartrate moiety influences the diastereoselectivity of the resultant sulfinamides formed in the reaction. The formed products serve as excellent building blocks for the synthesis of natural products. This has been demonstrated in the collective total synthesis of lentiginosine, (+)-α-conhydrine and methyldihydropalustramate.

CYCLIZED SULFAMOYLARYLAMIDE DERIVATIVES AND THE USE THEREOF AS MEDICAMENTS FOR THE TREATMENT OF HEPATITIS B

Inhibitors of HBV replication of Formula (I-A), including stereochemically isomeric forms, and salts, hydrates, solvates thereof, wherein Ra to Rd, and R1 to R8 have the meaning as defined herein. The present invention also relates to processes for preparing said compounds, pharmaceutical compositions containing them and their use, alone or in combination with other HBV inhibitors, in HBV therapy.

DDQ-Promoted Benzylic/Allylic sp3 C-H Activation for the Stereoselective Intramolecular C-N Bond Formation: Applications to the Total Synthesis of (-)-Codonopsinine, (+)-5-epi-Codonopsinine, (+)-Radicamine B, and (-)-Codonopsinol

This is the first report on an intramolecular C-N bond formation of an amide-tethered benzylic/allylic system using DDQ under neutral conditions which has been successfully applied to the total synthesis of naturally occurring pyrolidine alkaloids. The key steps for the synthesis of corresponding precursors involve Julia-Kociensky olefination/cross-metathesis and dihydroxylation reactions, and this methodology is also extended to the ω-unsaturated N-sulfanilamide to furnish piperidines.

METHOD OF PRODUCING PYRAZINO[2,1-C][1,2,4]TRIAZINE COMPOUND

A method of producing 4-(((6S,9S)-1-(benzylcarbamoyl)-2,9-dimethyl-4,7-dioxo-8-(quinolin-8-ylmethyl)octahydro -1H-pyrazino[2,1-c][1,2,4]triazin-6-yl)methyl)phenyl dihydrogen phosphate, including a step of adding a reaction mixture 1 containing (6S,9S)-N-b