112196-57-3

Usage

Chemical Properties

Colourless Oil

InChI:InChI=1/C21H35NO5Si/c1-20(2,3)26-19(24)22-17(18(23)25-7)14-15-10-12-16(13-11-15)27-28(8,9)21(4,5)6/h10-13,17H,14H2,1-9H3,(H,22,24)/t17-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 60-18-4 L-tyrosine 
• 1080-06-4 L-Tyr-OMe 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 179680-94-5 {(S)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-1-hydroxymethyl-ethyl}-carbamic acid tert-butyl ester 
• 110071-96-0 sodium salt of tert-butyloxycarbonyl-O-sulfotyrosine α-methyl ester 
• 94732-15-7 (S)-2-(2-N-tert-butoxycarbonylamino)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-propanoic acid 
• 112196-64-2 2-{[(S)-2-({(S)-2-[(S)-2-{[(S)-2-((R)-2-Amino-propionylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionylamino]-propionyl}-methyl-amino)-3-(4-hydroxy-phenyl)-propionyl]-methyl-amino}-3-(4-hydroxy-phenyl)-propionic acid; compound with trifluoro-acetic acid 
• 112196-65-3 C₅₁H₅₉F₅N₆O₁₂ 
• 112196-61-9 Boc-D-Ala-Ala-N-Me-Tyr(OMe)-Ala-N-Me-Tyr-N-Me-Tyr-OMe 
• 112196-62-0 Boc-D-Ala-Ala-N-Me-Tyr(OMe)-Ala-N-Me-Tyr-N-Me-Tyr-OH 

Relevant academic research and scientific papers

COMPOUNDS COMPRISING CLEAVABLE LINKER AND USES THEREOF

Provided are a compound including a cleavable linker, a use thereof, and an intermediate compound for preparing the same, and more particularly, the compound including a cleavable linker of the present invention may include an active agent (for example, a drug, a toxin, a ligand, a probe for detection, etc.) having a specific function or activity, a -S(=0)(=N-)- functional group which is capable of selectively releasing the active agent, and a functional group which triggers a chemical reaction, a physicochemical reaction and/or a biological reaction by external stimulation, and may further include a ligand (for example, oligopeptide, polypeptide, antibody, etc.) having binding specificity for a desired target receptor.

A General Approach to O-Sulfation by a Sulfur(VI) Fluoride Exchange Reaction

O-sulfation is an important chemical code widely existing in bioactive molecules, but the scalable and facile synthesis of complex bioactive molecules carrying O-sulfates remains challenging. Reported here is a general approach to O-sulfation by the sulfur(VI) fluoride exchange (SuFEx) reaction between aryl fluorosulfates and silylated hydroxy groups. Efficient sulfate diester formation was achieved through systematic optimization of the electronic properties of aryl fluorosulfates. The versatility of this O-sulfation strategy was demonstrated in the scalable syntheses of a variety of complex molecules carrying sulfate diesters at various positions, including monosaccharides, disaccharides, an amino acid, and a steroid. Selective hydrolytic and hydrogenolytic removal of the aryl masking groups from sulfate diesters yielded the corresponding O-sulfate products in excellent yields. This strategy provides a powerful tool for the synthesis of O-sulfate bioactive compounds.

Tertiary-butoxycarbonyl (Boc) – A strategic group for N-protection/deprotection in the synthesis of various natural/unnatural N-unprotected aminoacid cyanomethyl esters

A number of cyanomethyl esters of natural/unnatural aminoacids with un-protected amino functionality were synthesized because of their synthetic and medicinal importance. Critical N-Boc deprotection methods in the presence of labile (hydrolytic sensitivity) cyanomethyl functionality were screened thoroughly and it was found that readily available 4M HCl in 1,4-dioxane solution (2–4 equiv); acetonitrile, 0 °C, 2–4 h was a suitable condition. This condition was generalized and successfully applied to a variety of alkyl, alkynyl, aryl, heteroaryl, benzyl, azido, spiro amino acid cyanomethylesters irrespective of the nature of the amine (primary or secondary) and the distance between the amine and ester group to achieve final deprotected amino esters with high yield, and purity compared to other commonly known N-protecting groups (Cbz, Fmoc, Ac, Bn, Bz etc.). It was also demonstrated that N-Boc protected aminoacid cyanomethylesters are stable enough to carry out further functionalization compared to N-unprotected counterparts.

TYROSINE AMIDE DERIVATIVES AS RHO- KINASE INHIBITORS

Bicyclic dihydropyrimidine-carboxamide compounds of formula I described herein inhibit Rho Kinase and may be used for the treatment of many disorders associated with ROCK enzymes mechanisms, such as pulmonary diseases including asthma, chronic obstructive pulmonary disease (COPD), idiopathic pulmonary fibrosis (IPF) and pulmonary arterial hypertension (PAH).

Improved binding affinities of pyrrolidine derivatives as Mcl-1 inhibitors by modifying amino acid side chains

As an important member of anti-apoptotic Bcl-2 protein, myeloid cell leukemia sequence 1 (Mcl-1) protein is an attractive target for cancer therapy. In this study, a new series of pyrrolidine derivatives as Mcl-1 inhibitors were developed by mainly modifying the amino acid side chain of compound 1. Among them, compound 18 (Ki= 0.077 μM) exhibited better potent inhibitory activities towards Mcl-1 protein compared to positive control Gossypol (Ki= 0.18 μM). In addition, compound 40 possessed good antiproliferative activities against PC-3 cells (Ki= 8.45 μM), which was the same as positive control Gossypol (Ki= 7.54 μM).

Diphenyl sulfate derivatives, preparation method of thereof and fluorophore sensor comprising thereof

The present invention relates to a diphenyl sulfate derivative, a method for preparing the same, and a fluorescence bio-sensor comprising the same. The diphenyl sulfate derivative having a novel structure according to the present invention traces cells and carries out immuno-fluorescence staining of the mitochondria of the cells satisfactorily. Thus, the diphenyl sulfate sulfate is useful in the glioma-related field and the research field including virus and DNA transfection, and can be used advisably as fluorescence bio-sensor for diagnosing diseases, such as glioma, sarcoma or leukemia.

Synthesis of MeO-PEG2000-supported chiral ferrocenyl oxazoline carbinol ligand and its application in asymmetric catalysis

A simple method for the synthesis of a MeO-PEG-supported chiral ferrocenyl oxazoline carbinol ligand has been developed. The chiral ligand was successfully applied to the catalytic asymmetric addition of diethylzinc to aryl aldehydes, affording secondary alcohols in high yields and with excellent enantioselectivities (up to 94% ee). The chiral ligand can be recovered and reused twice with no apparent loss of catalyst efficiency.

The total synthesis of the diepoxycyclohexanone antibiotic aranorosin and novel synthetic analogues

A short synthesis of the novel antibiotic aranorosin in chiral form is described which employs (i) a novel hypervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative and (ii) a stereocontrolled cis-bisepoxidation in the key steps. A similar procedure was employed to prepare 6′-epiaranorosin, and hence establish the stereochemistry of the natural compound, and to prepare novel aranorosin analogues. An organometallic route is described which gives desamidoaranorosin.