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 
• 70277-02-0 3-iodo-L-tyrosine methyl ester 
• 121778-71-0 (S)-2-(benzyloxycarbonylamino)-3-(4-methoxyphenyl)-1-propionic acid methyl ester 
• 60-18-4 L-tyrosine 
• 79677-58-0 2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride 
• 79677-60-4 (S)-N-benzyloxycarbonyl-3-(4-hydroxy-3-iodophenyl)alanine methyl ester 
• 501-53-1 benzyl chloroformate 

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 
• 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 
• 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 

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.

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

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 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).