112196-57-3

Basic information

• Product Name: O-TERT-BUTYLDIMETHYLSILYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER
• Synonyms: O-TERT-BUTYLDIMETHYLSILYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER;N-[(1,1-DiMethylethoxy)carbonyl]-O-[(1,1-diMethylethyl)diMethylsilyl]-L-tyrosine Methyl Ester
• CAS NO: 112196-57-3
• Molecular Formula: C₂₁H₃₅NO₅Si
• Molecular Weight: 409.5918
• Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives
• Mol File: 112196-57-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 468.468°C at 760 mmHg
• Flash Point: 237.121°C
• Appearance: /
• Density: 1.033g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.486
• Solubility: Ethyl Acetate, Methanol
• PKA: 11.02±0.46(Predicted)
• CAS DataBase Reference: O-TERT-BUTYLDIMETHYLSILYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: O-TERT-BUTYLDIMETHYLSILYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER(112196-57-3)
• EPA Substance Registry System: O-TERT-BUTYLDIMETHYLSILYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER(112196-57-3)

Safety Data

• Hazardous Substances Data: 112196-57-3(Hazardous Substances Data)

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

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

Downstream Products

• 112196-58-4 (S)-methyl-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-((tert-butyldimethyl-silyl)oxy)phenyl)propanoate 
• 179680-94-5 {(S)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-1-hydroxymethyl-ethyl}-carbamic acid tert-butyl ester 
• 149451-90-1 {(S)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-1-formyl-ethyl}-carbamic acid tert-butyl ester 
• 70963-39-2 N-methyl-L-tyrosine methyl ester 
• 82038-34-4 (S)-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-hydroxyphenyl)propanoic acid 
• 112196-67-5 C₄₆H₅₁F₅N₆O₁₀*C₂HF₃O₂ 
• 112196-59-5 methyl N-(tert-butoxycarbonyl)-N-methyl-L-tyrosinate 
• 112196-60-8 H-N-Me-Tyr-N-Me-Tyr-OMe 
• 84254-47-7 methyl N-boc-N-methyl-L-tyr-N-methyl-L-tyrosinate 
• 91502-34-0 cyclo-N-methyl-L-tyr-N-methyl-L-tyr-D-ala-L-ala-O,N-dimethyl-L-tyr-L-ala 
• 112196-62-0 Boc-D-Ala-Ala-N-Me-Tyr(OMe)-Ala-N-Me-Tyr-N-Me-Tyr-OH 
• 112196-61-9 Boc-D-Ala-Ala-N-Me-Tyr(OMe)-Ala-N-Me-Tyr-N-Me-Tyr-OMe 
• 112196-65-3 C₅₁H₅₉F₅N₆O₁₂ 
• 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 

Relevant articles and documents

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.

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.

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).