Boc-D-tyr(ME)-OH

Base Information

• Chemical Name: Boc-D-tyr(ME)-OH
• CAS No.: 68856-96-2
• Molecular Formula: C15H21 N O5
• Molecular Weight: 295.335
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID10426919
• Nikkaji Number: J1.248.626J
• Wikidata: Q72510265
• Mol file: 68856-96-2.mol

Synonyms:BOC-D-TYR(ME)-OH;68856-96-2;BOC-O-METHYL-D-TYROSINE;(2R)-3-(4-methoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;Boc-4-Methoxy-D-Phenylalanine;N-Boc-4-methoxy-D-phenylalanine;D-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl-;(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoic acid;(R)-2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoic acid;Boc-4-methoxy-D-Phe-OH;MFCD00065604;Boc-D-Phe(4-OMe)-OH;Boc-L-phe(4-OCH3)-OH;SCHEMBL1308867;DTXSID10426919;SLWWWZWJISHVOU-GFCCVEGCSA-N;AKOS015836435;AKOS015907893;CS-W009976;DS-9763;HY-W009260;AC-25340;B5350;N-(tert-butoxycarbonyl)-O-methyl-D-tyrosine;N-alpha-t-butoxycarbonyl-o-nethyl-D-tyrosine;EN300-70250;N10794;N-(tert-Butoxycarbonyl)-4-methoxy-D-phenylalanine;(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid;(R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoic acid;(R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionic acid;(R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoic acid;(R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid;(R)-alpha-(tert-Butoxycarbonylamino)-4-methoxyhydrocinnamic acid;N-tert.-Butoxycarbonyl-2-(R)-amino-3-(4-methoxyphenyl)-propionic acid

Chemical Property of Boc-D-tyr(ME)-OH

Chemical Property:

• Melting Point: 93.0 to 97.0 °C
• Boiling Point: 462.0±40.0 °C(Predicted)
• PKA: 3.00±0.10(Predicted)
• PSA: 84.86000
• Density: 1.168±0.06 g/cm3(Predicted)
• 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% ^*data from raw suppliers

Boc-O-methyl-D-tyrosine ^*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-O-methyl-D-tyrosine is a compound involved in the design and synthesis of β-sheet-based self-assembling cyclic peptides with tunable cavities.

Technology Process of Boc-D-tyr(ME)-OH

There total 15 articles about Boc-D-tyr(ME)-OH 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: 88.0%

(2R)-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid methyl ester (94790-24-6) → N-(tert-butoxycarbonyl)-O-methyl-D-tyrosine (68856-96-2)

Guidance literature:

With water; potassium carbonate; In methanol; for 12h;

DOI:10.1016/j.tetlet.2012.10.078

Reference yield:

N-tert.-butoxycarbonyl-2-(R)-amino-3-(4-methoxyphenyl)-propionic acid benzyl ester (215454-88-9) → N-(tert-butoxycarbonyl)-O-methyl-D-tyrosine (68856-96-2)

Guidance literature:

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-O-methyl-D-tyrosine (68856-96-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) K₂CO₃ / 1.) H₂O, 10 min, 2.) t-BuOH, ether, 25 min

2: K₂CO₃, 18-crown-6 / benzene / 1.5 h / Heating

3: NaOH / methanol; H₂O / 0.5 h

With sodium hydroxide; 18-crown-6 ether; potassium carbonate; In methanol; water; benzene;

DOI:10.1021/jo00322a049

upstream raw materials:

(2R)-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid methyl ester

di-tert-butyl dicarbonate

tyrosine

N-(tert-butoxycarbonyl)-D-tyrosine methyl ester

Downstream raw materials:

(S)-3-[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-2-methyl-propionic acid

3-[(2R)-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoic acid

benzyl (2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionylamino]-propionyloxy]-4-methylpentanoate

(R)-4-methoxyphenylalanine methyl ester hydrochloride

Refernces

• 1、 Blake, James F.,Kallan, Nicholas C.,Xiao, Dengming,Xu, Rui,Bencsik, Josef R.,Skelton, Nicholas J.,Spencer, Keith L.,Mitchell, Ian S.,Woessner, Richard D.,Gloor, Susan L.,Risom, Tyler,Gross, Stefan D.,Martinson, Matthew,Morales, Tony H.,Vigers, Guy P.A.,Brandhuber, Barbara J.. "Discovery of pyrrolopyrimidine inhibitors of Akt". scheme or table. p. 5607 - 5612. Retrieved 2010/11/17.
• 2、 Kolodziejczyk,Manning. "A convenient method for O-alkylation of N-substituted tyrosines using a crown ether". . p. 1944 - 1946. Retrieved 2007/10/02.