Fmoc-O-Methyl-D-Tyrosine

Base Information

• Chemical Name: Fmoc-O-Methyl-D-Tyrosine
• CAS No.: 201335-88-8
• Molecular Formula: C₂₅H₂₃NO₅
• Molecular Weight: 417.461
• DSSTox Substance ID: DTXSID30427180
• Wikidata: Q72478588
• Mol file: 201335-88-8.mol

Synonyms:201335-88-8;FMOC-D-TYR(ME)-OH;Fmoc-O-Methyl-D-Tyrosine;Fmoc-4-Methoxy-D-Phenylalanine;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-methoxyphenyl)propanoic acid;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-methoxyphenyl)propanoic acid;FMOC-4-METHOXY-D-PHE-OH;SCHEMBL2310128;DTXSID30427180;D-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-methyl-;Fmoc-D-Tyr(Me)-OH, AldrichCPR;MFCD00237393;AKOS015837397;HY-W022227;DS-13636;CS-0040948;A50176;EN300-3395151;J-013041;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-methoxyphenyl)propanoic acid

Chemical Property of Fmoc-O-Methyl-D-Tyrosine

Chemical Property:

• Vapor Pressure: 1.15E-17mmHg at 25°C
• Melting Point: 647.8 °C at 760 mmHg
• Refractive Index: 1.62
• Boiling Point: 647.8oC at 760 mmHg
• PKA: 2.97±0.10(Predicted)
• Flash Point: 345.6 °C
• PSA: 76.07000
• Density: 1.274 g/cm³
• LogP: 4.52930
• Storage Temp.: Store at RT.
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 417.15762283
• Heavy Atom Count: 31
• Complexity: 595

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-O-methyl-D-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: COC1=CC=C(C=C1)C[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of Fmoc-O-Methyl-D-Tyrosine

There total 8 articles about Fmoc-O-Methyl-D-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: 96.0%

Fmoc-Tyr(OMe)-OMe → N-(9-fluorenylmethoxycarbonyl)-O-methyl-L-tyrosine (77128-72-4,201335-88-8)

Guidance literature:

With magnesium iodide; In tetrahydrofuran; at 120 ℃; for 1h; chemoselective reaction; Inert atmosphere; Microwave irradiation; Sealed tube;

DOI:10.1002/chem.201501799

Reference yield: 92.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + O-methyl-L-tyrosine (3308-72-3,6230-11-1,7635-29-2,39878-65-4) → N-(9-Fluorenylmethyloxy)carbonyl-O-methyl-L-tyrosine (77128-72-4,201335-88-8)

Guidance literature:

With sodium carbonate; In 1,4-dioxane;

DOI:10.1016/S0040-4020(01)81776-2

Reference yield: 64.0%

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(4'-methoxyphenyl)propionic acid tert-butyl ester (381222-43-1) → N-(9-fluorenylmethoxycarbonyl)-O-methyl-L-tyrosine (77128-72-4,201335-88-8)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1039/b103832j

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

O-methyl-L-tyrosine

O-Methyltyrosine

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Downstream raw materials:

[Phe(p-OMe)¹]-alloferon

Refernces

• 1、 Berthet, Mathéo,Davanier, Florian,Dujardin, Gilles,Martinez, Jean,Parrot, Isabelle. "MgI2-Mediated Chemoselective Cleavage of Protecting Groups: An Alternative to Conventional Deprotection Methodologies". supporting information. p. 11014 - 11016. Retrieved 2015/11/10.
• 2、 Motawia,Meldal,Sofan,Stein,Pedersen,Nielsen. "2'-Deoxypuromycin: Synthesis and antiviral evaluation". . p. 265 - 270. Retrieved 2007/10/02.