Boc-O-methyl-L-tyrosine

Base Information

• Chemical Name: Boc-O-methyl-L-tyrosine
• CAS No.: 53267-93-9
• Molecular Formula: C15H21NO5
• Molecular Weight: 295.335
• Hs Code.: 2924 29 70
• DSSTox Substance ID: DTXSID60376137
• Nikkaji Number: J1.035.047F
• Wikidata: Q72450087
• Mol file: 53267-93-9.mol

Synonyms:Boc-Tyr(Me)-OH;53267-93-9;Boc-O-methyl-L-tyrosine;(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-methoxyphenyl)propanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoic acid;Boc-4-Methoxyphenylalanine;Boc-D,L-Tyr(Me)-OH;(2S)-3-(4-methoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;Boc-4-Methoxy-L-Phenylalanine;L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl-;N-(tert-butoxycarbonyl)-O-methyltyrosine;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoic acid;BOC-4-METHOXY-PHE-OH;MFCD00065603;Boc-O-Methyl-Tyrosine;SCHEMBL335309;DTXSID60376137;SLWWWZWJISHVOU-LBPRGKRZSA-N;AKOS015836422;AM82324;CS-W009974;DS-1941;HY-W009258;AC-25339;N-tert-butoxycarbonyl-O-methyl-L-tyrosine;EN300-70849;M02118;N-ALPHA-T-BUTYLOXYCARBONYL-O-METHYL-L-TYROSINE;Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl-;(s)-2-(t-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoic acid;(s)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoic acid;(S)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID

Chemical Property of Boc-O-methyl-L-tyrosine

Chemical Property:

• Vapor Pressure: 2.47E-09mmHg at 25°C
• Refractive Index: 1.522
• Boiling Point: 462 °C at 760 mmHg
• PKA: 3.00±0.10(Predicted)
• Flash Point: 233.2 °C
• PSA: 84.86000
• Density: 1.168 g/cm³
• LogP: 2.60650
• Storage Temp.: Store at 0-5°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 295.14197277
• Heavy Atom Count: 21
• Complexity: 356

Purity/Quality:

99%min ^*data from raw suppliers

Boc-Tyr(Me)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)OC)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)OC)C(=O)O
• Uses: Boc-Tyr(Me)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of Boc-O-methyl-L-tyrosine

There total 15 articles about Boc-O-methyl-L-tyrosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N-(tert-butyloxycarbonyl) azide (1070-19-5) + O-Methyltyrosine (6230-11-1) → O-methyl-N-tert-butoxycarbonyl-L-tyrosine (53267-93-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 25 ℃; for 6h;

DOI:10.1021/jm00180a027

Reference yield: 98.0%

(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoate (94790-24-6) → O-methyl-N-tert-butoxycarbonyl-L-tyrosine (53267-93-9)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2014.06.108

Reference yield: 97.0%

Boc-Tyr-OH (3978-80-1) + methyl iodide (74-88-4) → O-methyl-N-tert-butoxycarbonyl-L-tyrosine (53267-93-9)

Guidance literature:

Boc-Tyr-OH; methyl iodide; With potassium carbonate; In acetone; for 18h; Reflux;

With methanol; sodium hydroxide; at 40 ℃; for 3h;

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

O-Methyltyrosine

(S)-2-amino-3-(4-methoxyphenyl)propanoic acid hydrochloride

(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoate

Downstream raw materials:

[(S)-2-hydroxy-1-(4-methoxybenzyl)ethyl]carbamic acid tert-butyl ester

N--O⁴-methyl-L-tyrosyl>-L-alanine methyl ester

9-<3-(N-tert-butoxycarbonyl-p-methoxyphenyl-L-alanyl)amino-2-fluoro-2,3-dideoxy-5-O-trityl-β-D-ribofuranosyl>-N⁶,N⁶-dimethyladenine

Boc-Tyr(Me)-Phe-Val-Asn-Cys(Bzl)-Pro-Arg(Tos)-Gly-NH₂

Refernces

• 1、 Lü, Zirui,Li, Xiaona,Niu, Yan,Sun, Qi,Wang, Chao,Xi, Dandan,Xu, Fengrong,Xu, Ping,Zhou, Tongliang. "Design and synthesis of tripeptidyl furylketones as selective inhibitors against the β5 subunit of human 20S proteasome". . . Retrieved 2020/03/10.
• 2、 Chen, Chen,Nie, Yiming,Xu, Guangsen,Yang, Xinying,Fang, Hao,Hou, Xuben. "Design, synthesis and preliminary bioactivity studies of indomethacin derivatives as Bcl-2/Mcl-1 dual inhibitors". . p. 2771 - 2783. Retrieved 2019/05/15.