Fmoc-N-Me-Tyr(tBu)-OH

Base Information

• Chemical Name: Fmoc-N-Me-Tyr(tBu)-OH
• CAS No.: 133373-24-7
• Molecular Formula: C29H31NO5
• Molecular Weight: 473.569
• Hs Code.: 2924 29 70
• European Community (EC) Number: 800-929-9
• DSSTox Substance ID: DTXSID40576956
• Wikidata: Q72503169
• Mol file: 133373-24-7.mol

Synonyms:133373-24-7;Fmoc-N-Me-Tyr(tBu)-OH;Fmoc-Nalpha-methyl-O-t-butyl-L-tyrosine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(4-(tert-butoxy)phenyl)propanoic acid;L-Tyrosine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-;(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoic acid;Fmoc-N-methyl-O-t-butyl-L-tyrosine;Fmoc-N-methyl-O-tert-butyl-L-tyrosine;Fmoc-N-Me-L-Tyr(tBu)-OH;MFCD02684471;Fmoc-MeTyr(tBu)-OH;SCHEMBL15632803;DTXSID40576956;AMY22688;Fmoc-N-Me-Tyr(tBu)-OH, 97%;fmoc-N-me-tyr(tbu)-oh, AldrichCPR;AKOS015837133;AKOS015907921;CS-W013831;(2S)-3-[4-(tert-butoxy)phenyl]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino}propanoic acid;AS-17231;A888122;J-006362;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-alpha-methyl-O-t-butyl-L-tyrosine;O-tert-Butyl-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-N-methyl-L-tyrosine;N-fluorenyl-methylen-xycarbonyl-O-tert-butyl-N-methyl-tyrosine;Fmoc-N-Me-Tyr(t-Bu)-OH;2-{[(9H-Fluoren-9-ylmethoxy)carbonyl](methyl)amino}-3-{4-[(2-hydroxypropan-2-yl)oxy]phenyl}propanoic acid

Chemical Property of Fmoc-N-Me-Tyr(tBu)-OH

Chemical Property:

• Melting Point: 186-191°C
• Boiling Point: 638.9 °C at 760 mmHg
• PKA: 2.98±0.10(Predicted)
• Flash Point: 340.2 °C
• PSA: 76.07000
• Density: 1.208 g/cm³
• LogP: 5.74050
• Storage Temp.: Store at 0-5°C
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 473.22022309
• Heavy Atom Count: 35
• Complexity: 703

Purity/Quality:

≥98%, ^*data from raw suppliers

Fmoc-N-methyl-O-tert-butyl-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC1=CC=C(C=C1)CC(C(=O)O)N(C)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: CC(C)(C)OC1=CC=C(C=C1)C[C@@H](C(=O)O)N(C)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of Fmoc-N-Me-Tyr(tBu)-OH

There total 3 articles about Fmoc-N-Me-Tyr(tBu)-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: 78.0%

N-methyl-N-nosyl-O-tert-butyl-L-tyrosine phenacyl ester (1208119-58-7) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-Fmoc-N-methyl-O-tert-butyl-L-tyrosine (133373-24-7,1799443-50-7)

Guidance literature:

N-methyl-N-nosyl-O-tert-butyl-L-tyrosine phenacyl ester; With sodium thiophenolate; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;

With sodium carbonate; In water; pH=9;

(fluorenylmethoxy)carbonyl chloride; In 1,4-dioxane; at 0 ℃;

DOI:10.1021/jo901643f

Reference yield: 73.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Nα-nosyl-O-tert-butyl-L-tyrosine (941296-83-9) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-Fmoc-N-methyl-O-tert-butyl-L-tyrosine (133373-24-7,1799443-50-7)

Guidance literature:

Multistep reaction.;

DOI:10.1021/jo070075m

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (S)-3-(4-tert-Butoxy-phenyl)-2-methylamino-propionic acid (343631-38-9) → N-Fmoc-N-methyl-O-tert-butyl-L-tyrosine (133373-24-7,1799443-50-7)

Guidance literature:

With aq. NaCO₃; In 1,4-dioxane; at 0 ℃; Yield given;

DOI:10.1021/jm00110a005

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(S)-3-(4-tert-Butoxy-phenyl)-2-methylamino-propionic acid

diazomethane

N^α-nosyl-O-tert-butyl-L-tyrosine

Downstream raw materials:

H-Arg-Arg-Pro-N-Me-Tyr-Ile-Leu-OH

Refernces

• 1、 Di Gioia, Maria Luisa,Leggio, Antonella,Liguori, Angelo,Perri, Francesca. "Solid-phase synthesis of N-nosyl- and N-Fmoc-N-methyl-α-amino acids". . p. 3723 - 3728. Retrieved 2008/02/05.