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

Base Information

• Chemical Name: L-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2,6-dimethyl-, methyl ester
• CAS No.: 503186-53-6
• Molecular Formula: C27H27NO5
• Molecular Weight: 445.515
• Mol file: 503186-53-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 1 articles about L-Tyrosine, 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:

methanol (67-56-1) + (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoic acid → Fmoc-2,6-dimethyl-(L)-Tyr-OMe (503186-53-6)

Guidance literature:

With thionyl chloride; for 1.5h;

DOI:10.1021/jm025608s

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:

Fmoc-2,6-dimethyl-(L)-Tyr-OMe (503186-53-6) → (4S,5S)-5-Allyl-4-(4-tert-butoxy-2,6-dimethyl-benzyl)-oxazolidin-2-one

Guidance literature:

Multi-step reaction with 6 steps

1.1: 71 percent / c. H₂SO₄ / CH₂Cl₂ / 258.58 Torr

2.1: NHMe₂ / tetrahydrofuran / 1 h

3.1: 302 mg / Et₃N / tetrahydrofuran / 1 h

4.1: DIBAL-H / toluene; various solvent(s) / 1 h / -78 °C

4.2: Rochelle's salt / toluene; various solvent(s) / 1 h

5.1: 38 mg / tetrahydrofuran; diethyl ether / 4 h / 0 °C

6.1: BuLi; KBr / tetrahydrofuran

With n-butyllithium; sulfuric acid; diisobutylaluminium hydride; dimethyl amine; triethylamine; potassium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jm025608s

upstream raw materials:

methanol

Downstream raw materials:

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

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

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.