L-Tyrosine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2,6-dimethyl -, methyl ester

Base Information

• Chemical Name: L-Tyrosine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2,6-dimethyl -, methyl ester
• CAS No.: 503186-54-7
• Molecular Formula: C31H35NO5
• Molecular Weight: 501.623
• Mol file: 503186-54-7.mol

Synonyms:

Chemical Property of L-Tyrosine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2,6-dimethyl -, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Tyrosine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2,6-dimethyl -, methyl ester

There total 2 articles about L-Tyrosine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2,6-dimethyl -, methyl ester 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: 71.0%

isobutene (115-11-7,15220-85-6) + Fmoc-2,6-dimethyl-(L)-Tyr-OMe (503186-53-6) → Fmoc-2,6-dimethyl-(L)-Tyr(tBu)-OMe (503186-54-7)

Guidance literature:

With sulfuric acid; In dichloromethane; under 258.581 Torr;

DOI:10.1021/jm025608s

Reference yield:

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoic acid → Fmoc-2,6-dimethyl-(L)-Tyr(tBu)-OMe (503186-54-7)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 1.5 h

2: 71 percent / c. H₂SO₄ / CH₂Cl₂ / 258.58 Torr

With thionyl chloride; sulfuric acid; In dichloromethane;

DOI:10.1021/jm025608s

Reference yield: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + Fmoc-2,6-dimethyl-(L)-Tyr(tBu)-OMe (503186-54-7) → N-<(1,1-dimethylethoxy)carbonyl>-O-(1,1-dimethylethyl)-2,6-dimethyl-L-tyrosine methyl ester (137650-16-9)

Guidance literature:

Fmoc-2,6-dimethyl-(L)-Tyr(tBu)-OMe; With dimethyl amine; In tetrahydrofuran; for 1h;

di-tert-butyl dicarbonate; With triethylamine; In tetrahydrofuran; for 1h;

upstream raw materials:

isobutene

Fmoc-2,6-dimethyl-(L)-Tyr-OMe

Downstream raw materials:

1,1-dimethylethyl <2-<4-(1,1-dimethylethoxy)-2,6-dimethylphenyl>-1(S)-formylethyl>carbamate

N-<(1,1-dimethylethoxy)carbonyl>-O-(1,1-dimethylethyl)-2,6-dimethyl-L-tyrosine methyl ester

[1-(4-tert-butoxy-2,6-dimethyl-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester

2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-2,6-dimethyl-phenyl)-3,7-dihydroxy-non-4-enoic acid

Refernces

• 1、 Harrison, Bryce A.,Pasternak, Gavril W.,Verdine, Gregory L.. "2,6-Dimethyltyrosine analogues of a stereodiversified ligand library: Highly potent, selective, non-peptidic μ opioid receptor agonists". . p. 677 - 680. Retrieved 2007/10/03.