(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoic acid

Base Information

• Chemical Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoic acid
• CAS No.: 159751-47-0
• Molecular Formula: C25H29NO6
• Molecular Weight: 439.508
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID20575604
• Nikkaji Number: J2.240.264A
• Mol file: 159751-47-0.mol

Synonyms:159751-47-0;Fmoc-Aad(otBu)-OH;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoic acid;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxy]-6-oxohexanoic acid;Fmoc-L-alpha-aminoadipic acid delta-tert-butyl ester;(S)-2-(Fmoc-Amino)-Hexanedioic Acid-6-T-Butyl Ester;Fmoc-L-Aad(OtBu)-OH;MFCD00237006;C25H29NO6;FFLAQPKWVSSKJC-NRFANRHFSA-N;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-tert-butoxy-6-oxohexanoic acid;SCHEMBL16060615;DTXSID20575604;AKOS015911933;DS-13370;CS-0101115;F12306;J-009640;(S)-2-(Fmoc-amino)-6-(tert-butoxy)-6-oxohexanoic acid;(S)-2-(Fmoc-amino)adipic acid 6-t-butyl ester (Fmoc-L-Aad(tBu)-OH);6-tert-Butoxy-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-6-oxo-L-norleucine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoicacid;Fmoc--aminoadipic acid--t-butyl ester;(S)-2-(Fmoc-amino)-hexanedioic acid-6-t-butyl ester;Fmoc-Homoglu(OtBu)-OH

Chemical Property of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoic acid

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.64E-16mmHg at 25°C
• Melting Point: 108-112 °C
• Refractive Index: 1.566
• Boiling Point: 625.546 °C at 760 mmHg
• PKA: 3.81±0.21(Predicted)
• Flash Point: 332.118 °C
• PSA: 101.93000
• Density: 1.215 g/cm³
• LogP: 4.88120
• Storage Temp.: 2-8°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 439.19948764
• Heavy Atom Count: 32
• Complexity: 650

Purity/Quality:

98% ^*data from raw suppliers

Fmoc-L-alpha-aminoadipic acid δ-tert-butyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)CCC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoic acid

There total 4 articles about (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoic 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: 96.0%

5-(9H-fluoren-9-ylmethoxycarbonylamino)-hex-2-enedioic acid 6-benzyl ester 1-tert-butyl ester (868754-93-2) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoic acid (159751-47-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1h;

DOI:10.1021/ol0520222

Reference yield:

tert-Butyl acrylate (1663-39-4,25232-27-3) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoic acid (159751-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / (PCy₃)Cl₂(C₃H₅N₂Mes₂)Ru=CHPh / CH₂Cl₂ / 2 h / Heating

2: 96 percent / H₂ / Pd/C / ethanol / 1 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogen; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/ol0520222

Reference yield:

2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid (146549-21-5) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoic acid (159751-47-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / NaHCO₃ / dimethylformamide

2: 87 percent / (PCy₃)Cl₂(C₃H₅N₂Mes₂)Ru=CHPh / CH₂Cl₂ / 2 h / Heating

3: 96 percent / H₂ / Pd/C / ethanol / 1 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0520222

upstream raw materials:

5-(9H-fluoren-9-ylmethoxycarbonylamino)-hex-2-enedioic acid 6-benzyl ester 1-tert-butyl ester

tert-Butyl acrylate

2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid

benzyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-4-enoate

Downstream raw materials:

C₇₂H₁₀₇N₁₅O₁₈S

Refernces