119336-08-2

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 71400-63-0 N-tert-butyloxycarbonyl-3-iodo-L-tyrosine 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 79677-58-0 2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride 
• 67-56-1 methanol 
• 70-78-0 3-Iodo-L-tyrosine 
• 344427-87-8 3-iodo-4-O-methoxymethyl-N-t-butoxycarbonyl-L-tyrosine methyl ester 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 998-40-3 tributylphosphine 
• 2622-14-2 tricyclohexylphosphine 
• 70277-02-0 3-iodo-L-tyrosine methyl ester 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 25799-58-0 (R)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid 
• 556-02-5 tyrosine 

Downstream Products

• 367967-63-3 N-[(1,1-dimethylethoxy)carbonyl]-3-formyl-L-tyrosine methyl ester 
• 930273-90-8 2-tert-butoxycarbonylamino-3-(4-methoxy-3-vinyl-phenyl)-propionic acid methyl ester 
• 926292-85-5 2-tert-butoxycarbonylamino-3-[3-(2-hydroxy-ethyl)-4-methoxy-phenyl]-propionic acid methyl ester 
• 926292-80-0 2-tert-butoxycarbonylamino-3-(4-methoxymethoxy-3-vinyl-phenyl)-propionic acid methyl ester 
• 926292-81-1 3-(3-allyl-4-methoxymethoxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 
• 926292-83-3 2-tert-butoxycarbonylamino-3-[3-(2-hydroxy-ethyl)-4-methoxymethoxy-phenyl]-propionic acid methyl ester 
• 926292-84-4 2-tert-butoxycarbonylamino-3-[3-(3-hydroxy-propyl)-4-methoxymethoxy-phenyl]-propionic acid methyl ester 
• 926292-82-2 3-(3-allyl-4-methoxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 
• 926292-86-6 2-tert-butoxycarbonylamino-3-[3-(3-hydroxy-propyl)-4-methoxy-phenyl]-propionic acid methyl ester 
• 926292-90-2 2-tert-butoxycarbonylamino-3-{4-methoxy-3-[3-(toluene-4-sulfonyloxy)-propyl]-phenyl}-propionic acid methyl ester 
• 367967-67-7 N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-O-(phenylmethyl)-L-tyrosine methyl ester 
• 367967-65-5 N-[(1,1-dimethylethoxy)carbonyl]-3-formyl-O-(phenylmethyl)-L-tyrosine methyl ester 
• 1027143-47-0 3-(4-benzyloxy-3-formyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 
• 691394-91-9 methyl (S)-3-(4-(benzyloxy)-3-iodophenyl)-2-((tert-butoxycarbonyl)amino)propanoate 

Relevant academic research and scientific papers

Stereoselective Oxa-Michael Addition of Tyrosine to Propargyl Aldehyde/Esters: Formation of Benzofurans and Flavones

The steroselective oxa-Michael addition of the phenol moiety present in tyrosine and 3-iodotyrosine to different propargyl aldehydes delivered products with predominantly Z stereochemistry, as evidenced by X-ray crystallography analysis. When ethyl propiolate was used as the propargyl ester source, the products were achieved with exclusively E stereochemistry with yields ranging from 17% to 91%. The oxa-Michael addition compounds served as substrates in the synthesis of 5- and 6-membered heterocyclic compounds. The atmosphere applied to the reaction medium directly influenced the formation of the products. When an inert atmosphere of nitrogen was applied, a 2-aryl-3-formyl-5-alanylbenzofuran core was selectively obtained via a Heck intramolecular reaction, while the reactions carried out under a carbon monoxide atmosphere led exclusively to 6-alanyl-2-arylflavone derivatives via reductive intramolecular acylation. (Figure presented.).

Tyrosine-derived stimuli responsive, fluorescent amino acids

A series of fluorescent unnatural amino acids (UAAs) bearing stilbene and meta-phenylenevinylene (m-PPV) backbone have been synthesized and their optical properties were studied. These novel UAAs were derived from protected diiodo-l-tyrosine using palladi

Late-Stage Functionalization of Peptides and Cyclopeptides Using Organozinc Reagents

We report a new late-stage functionalization of small peptides and cyclopeptides relying on the Negishi cross-coupling of readily prepared iodotyrosine- or iodophenylalanine-containing peptides with aryl-, heteroaryl-, and alkylzinc pivalates or halides.

Synthesis of biphenyl tyrosine via cross-coupling Suzuki-Miyaura reaction using aryltrifluoroborate salts

We reported a fast and easy method for obtaining biarylic units from tyrosine derivatives via Suzuki-Miyaura cross-coupling using a variety of substituted and unsubstituted potassium aryl- and heteroaryltrifluoroborate salts. The scope of the methodology

Synthesis of Pentacyclic Framework of Herquline A

The highly strained bowl-shaped pentacyclic structure of herquline A has rendered it one of the most difficult problems in organic synthesis yet to be solved. The challenges associated with the synthesis of herquline A have been well documented in four Ph.D. dissertations and in multiple reports regarding syntheses of its structurally simpler congeners. Herein, we report the construction of the pentacyclic core of herquline A that contains both N10?C2 and C3?C3′ bonds. The key for success was the development of the tandem aza-Michael addition/enolate capture protocol that set the stage for subsequent palladium catalyzed C3(sp2)?C3′(sp2) coupling reaction. Ensuing oxidative dearomatization of the left aryl ring allowed the formation of the pentacyclic diketone core of herquline A.

Method for preparing methyl 3-halogenated-N-protected-L-tyrosine ester

The invention discloses a method for preparing methyl 3-halogenated-N-protected-L-tyrosine ester, and belongs to the technical field of organic synthesis. The method comprises the steps: performing areaction between methyl N-protected-L-tyrosine ester and

Method for synthesizing 3-iodine-N-protected-L-tyrosine methyl ester through de-MOM-protection

The invention discloses a method for synthesizing 3-iodine-N-protected-L-tyrosine methyl ester through de-MOM-protection and belongs to the technical field of organic synthesis. N-protected-L-tyrosinemethyl ester is reacted with MOMCl and iodine reagent to give 3-iodine-N-protected-O-methyl methyl ether-L-tyrosine methyl ester, normal-pressure de-MOM-protection is performed in hydrogen atmosphereunder palladium catalysis to obtain 3-iodine-N-protected-L-tyrosine methyl ester. The method for removing the MOM protecting group adopted by the invention avoids the group tolerance problem in the conventional strong acid system such as hydrochloric acid, acetic acid, trifluoroacetic acid or boron trifluoride ether, and has high reaction selectivity and simple post-treatment.

Synthesis of the polyketide section of seragamide A and related cyclodepsipeptides via Negishi cross coupling

The synthesis of the polyketide section present in the potently cytotoxic marine cyclodepsipeptide jasplakinolide and related natural products, geodiamolides and seragamides, is reported. The key step is a Negishi cross coupling of (R)-(3-methoxy-2-methyl

Scalable Synthesis of Mycocyclosin

We report herein the scalable total synthesis of the secondary metabolite, mycocyclosin, initially isolated from Mycobacterium tuberculosis. Mycocylosin bears a highly strained 3,3′-dityrosine biaryl system which arises biosynthetically from an intramolec

Formal Total Synthesis of Diazonamide A by Indole Oxidative Rearrangement

A short formal total synthesis of the marine natural product diazonamide A is described. The route is based on indole oxidative rearrangement, and a number of options were investigated involving migration of tyrosine or oxazole fragments upon oxidation of open chain or macrocyclic precursors. The final route proceeds from 7-bromoindole by sequential palladium-catalysed couplings of an oxazole fragment at C-2, followed by a tyrosine fragment at C-3. With the key 2,3-disubstituted indole readily in hand, formation of a macrocyclic lactam set the stage for the crucial oxidative rearrangement to a 3,3-disubstituted oxindole. Notwithstanding the concomitant formation of the unwanted indoxyl isomer, the synthesis successfully delivered, after deprotection, the key oxindole intermediate, thereby completing a formal total synthesis of diazonamide A.