(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-7-((tert-butoxycarbonyl)amino)heptanoic acid

Base Information

• Chemical Name: (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-7-((tert-butoxycarbonyl)amino)heptanoic acid
• CAS No.: 203854-47-1
• Molecular Formula: C27H34 N2 O6
• Molecular Weight: 482.577
• European Community (EC) Number: 861-019-5
• DSSTox Substance ID: DTXSID10375817
• Nikkaji Number: J937.553H
• Wikidata: Q72509802
• Mol file: 203854-47-1.mol

Synonyms:203854-47-1;fmoc-l-beta-homolysine(boc);(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-7-((tert-butoxycarbonyl)amino)heptanoic acid;fmoc-l-nw-boc-beta-homolysine;Fmoc-|A-HoLys(Boc)-OH;(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-7-[(2-methylpropan-2-yl)oxycarbonylamino]heptanoic acid;(3S)-7-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]heptanoic acid;MFCD01863054;Fmoc-L-beta-HLys(Boc)-OH;Heptanoic acid, 7-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (3S)-;Fmoc-Lys(Boc)-(C#CH2)OH;CS-WAA0082;SCHEMBL4600617;DTXSID10375817;AKOS015900978;AM84928;AC-22082;AS-47150;CS-0035350;F12327;Fmoc-beta-Homolys(Boc)-OH, >=95.0% (HPLC);(S)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-7-(tert-butoxycarbonylamino)heptanoic acid;(S)-7-tert-Butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)-heptanoic acid;(3S)-7-[(tert-Butoxycarbonyl)amino]-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)heptanoic acid;(S)-7-[(tert-Butoxycarbonyl)amino]-3-[[[(9H-fluoren-9-yl)methoxy]carbonyl]amino]heptanoic acid

Chemical Property of (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-7-((tert-butoxycarbonyl)amino)heptanoic acid

Chemical Property:

• Vapor Pressure: 2.4E-20mmHg at 25°C
• Melting Point: 96℃
• Boiling Point: 696.2oC at 760 mmHg
• PKA: 4.39±0.10(Predicted)
• Flash Point: 374.8oC
• PSA: 113.96000
• Density: 1.195g/cm3
• LogP: 5.84520
• Storage Temp.: 2-8°C
• Water Solubility.: Sparingly soluble bin water.
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 482.24168681
• Heavy Atom Count: 35
• Complexity: 699

Purity/Quality:

97% ^*data from raw suppliers

Nbeta-Fmoc-Nω-Boc-L-beta-homolysine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCCCC(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)NCCCC[C@@H](CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: N(μ)-Boc-N(beta)-Fmoc-L-beta-homolysine is used as pharmaceutical intermediate. Fmoc-l-beta-homolysine(boc)

Technology Process of (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-7-((tert-butoxycarbonyl)amino)heptanoic acid

There total 5 articles about (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-7-((tert-butoxycarbonyl)amino)heptanoic acid 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: 81.0%

(S)-7-{[(tert-butoxy)carbonyl]amino}-1-diazo-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}heptane-2-one (203854-38-0) → Fmoc-(S)-β3-HLys(Boc)-OH (203854-47-1)

Guidance literature:

With 4-methyl-morpholine; silver trifluoroacetate; In tetrahydrofuran; water; for 3h;

DOI:10.1002/hlca.19980810202

Reference yield:

Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) → Fmoc-(S)-β3-HLys(Boc)-OH (203854-47-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N; i-BuOCOCl / tetrahydrofuran / 0.25 h / -25 °C

1.2: 89 percent / tetrahydrofuran; diethyl ether / 0 - 20 °C

2.1: 60 percent / CF₃COOAg; NMM / tetrahydrofuran; H₂O / 8 h / 0 - 20 °C

With 4-methyl-morpholine; silver trifluoroacetate; triethylamine; isobutyl chloroformate; In tetrahydrofuran; water; 2.1: Wolff rearrangement;

DOI:10.1021/jm010816q

Reference yield:

Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) → Fmoc-(S)-β3-HLys(Boc)-OH (203854-47-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / 1H-benzotriazol-1-yl-N-oxytrispyrrolidinophosphonium PF₆^(1-); N-ethyldiisopropylamine / tetrahydrofuran; dimethylformamide; diethyl ether / 0.25 h / 0 °C

2: 75 percent / silver benzoate / dioxane; H₂O / 70 °C

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; silver benzoate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; N,N-dimethyl-formamide; 2: Wolff rearrangement;

upstream raw materials:

(S)-7-{[(tert-butoxy)carbonyl]amino}-1-diazo-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}heptane-2-one

Fmoc-Lys(tert-butoxycarbonyl)