353520-75-9

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 353520-84-0 (S)-N-benzyloxycarbonyl-3-(3-iodo-4-methoxyphenyl)alanine methyl ester 
• 1080-06-4 L-Tyr-OMe 
• 13512-31-7 N-(benzyloxycarbonyl)-L-tyrosine methyl ester 
• 60-18-4 L-tyrosine 
• 121778-71-0 (S)-2-(benzyloxycarbonylamino)-3-(4-methoxyphenyl)-1-propionic acid methyl ester 
• 501-53-1 benzyl chloroformate 
• 79677-60-4 (S)-N-benzyloxycarbonyl-3-(4-hydroxy-3-iodophenyl)alanine methyl ester 
• 79677-58-0 2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride 
• 70277-02-0 3-iodo-L-tyrosine methyl ester 

Downstream Products

• 132513-32-7 3-hydroxy-O-methyl-N-<(phenylmethoxy)carbonyl>-L-tyrosine methyl ester 
• 1004524-43-9 C₄₃H₄₉N₃O₁₁ 
• 1004524-42-8 (S)-methyl 2-amino-3-(4-methoxy-3-(4,4,5 ,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)phenyl)propanoate 
• 612484-52-3 C₅₆H₇₆BBrN₈O₁₂ 
• 353520-92-0 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester 
• 353520-93-1 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester 
• 353520-90-8 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-triisopropylsilanyloxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester 
• 1054636-07-5 (S)-2-((S)-3-{3-[(S)-3-((1R,2R)-2-Amino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid 
• 353520-94-2 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-hydroxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester 
• 353520-86-2 2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-triisopropylsilanyloxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid methyl ester 
• 612484-59-0 (S)-2-Benzyloxycarbonylamino-3-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid 
• 443764-18-9 2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid 
• 353520-95-3 2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-triisopropylsilanyloxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid methyl ester 
• 443764-19-0 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester 

Relevant academic research and scientific papers

Structural and initial biological analysis of synthetic arylomycin A 2

The growing threat of untreatable bacterial infections has refocused efforts to identify new antibiotics, especially those acting by novel mechanisms. While the inhibition of pathogen proteases has proven to be a successful strategy for drug development,

Total synthesis of TMC-95A and -B via a new reaction leading to Z-enamides. Some preliminary findings as to SAR

A full account of the total syntheses of proteasome inhibitors TMC-95A and -B is provided. A key feature of the syntheses involved installation of a cis-propenylamide moiety by a thermal rearrangement of an α-silylallyl amide. The scope and mechanism of the enamide-forming reaction are discussed. Also provided are some preliminary results from SAR studies. It was found that simplified analogues can retain the full potency of proteasome inhibition.

Preparation of selectively protected L-dopa derivatives: Oxidation of tyrosine-3-boronates

Conversion of 3-iodo-L-tyrosine to protected tyrosine-3-boronate esters, followed by oxidation with hydrogen peroxide, provides a mild and efficient method for the preparation of selectively protected L-dopa derivatives.

Synthesis of a TMC-95A Ketomethylene Analogue by Cyclization via Intramolecular Suzuki Coupling

(Equation presented) A TMC-95A analogue extended at the C-terminus with NleΨ[COCH2]Gly-Ala-Ala-NH2 was synthesized via side-chain cyclization of the linear precursor by a Suzuki cross-coupling reaction in solution to analyze the effe

Synthesis of the functionalized macrocyclic core of proteasome inhibitors TMC-95A and B

An ordered assembly of four building blocks (2-5) forms the basis of the synthesis of 1, which contains the core structure of TMC-95A and B - two potent proteasome inhibitore (see scheme; TIPS = triisopropylsilyl, Cbz = benzoxycarbonyl, Boc = tert-Boc = tert-butoxycarbonyl).