(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)butanoic acid

Base Information

• Chemical Name: (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)butanoic acid
• CAS No.: 203854-51-7
• Molecular Formula: C23H27NO5
• Molecular Weight: 397.471
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID801129009
• Nikkaji Number: J937.555D
• Mol file: 203854-51-7.mol

Synonyms:203854-51-7;FMOC-L-BETA-HOMOSERINE(OTBU);Fmoc-O-t-butyl-L-beta-homoserine;(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)butanoic acid;Fmoc-|A-HoSer(tBu)-OH;(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]butanoic acid;fmoc-b-homo-ser(tbu)-oh;MFCD01862865;Butanoic acid, 4-(1,1-dimethylethoxy)-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (3R)-;Fmoc-HoSer(tBu)-OH;Fmoc--HoSer(tBu)-OH;Fmoc-L-beta-HSer(tBu)-OH;Fmoc-I(2)-HoSer(tBu)-OH;Fmoc-L-beta-HomoSer(tBu)-OH;Fmoc-Ser(tBu)-(C#CH2)OH;Fmoc-L-beta-Homo-Ser(OtBu)-OH;DTXSID801129009;AKOS015901005;DS-4581;AC-22093;CS-0035706;EN300-816427;Fmoc-beta-Homoser(tBu)-OH, >=97.5% (HPLC);J-013265;(R)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-tert-butoxybutanoic acid;(3R)-4-(1,1-Dimethylethoxy)-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid;(3R)-4-(tert-butoxy)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid;(r)-4-(1,1-dimethylethoxy)-3-((9h-fluoren-9-ylmethoxy)carbonylamino)butanoic acid

Chemical Property of (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)butanoic acid

Chemical Property:

• Vapor Pressure: 3.28E-15mmHg at 25°C
• Melting Point: 96-98℃
• Refractive Index: 1.569
• Boiling Point: 599.3 °C at 760 mmHg
• PKA: 4.27±0.10(Predicted)
• Flash Point: 316.2 °C
• PSA: 84.86000
• Density: 1.198 g/cm³
• LogP: 4.57440
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 397.18892296
• Heavy Atom Count: 29
• Complexity: 550

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-l-β-homoserine(otbu) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OCC(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC[C@@H](CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-l-beta-homoserine(otbu)

Technology Process of (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)butanoic acid

There total 3 articles about (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)butanoic 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: 74.0%

((S)-1-tert-Butoxymethyl-3-diazo-2-oxo-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (203854-41-5) → Fmoc-β3-O-t-butyl-L-homoserine (203854-51-7)

Guidance literature:

With silver benzoate; In 1,4-dioxane; water; at 70 ℃;

Reference yield:

Fmoc-Ser(tBu)-OH (71989-33-8) → Fmoc-β3-O-t-butyl-L-homoserine (203854-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) i-BuOCOCl, NMM / 1.) THF, -20 deg C, 20 min, 2.) THF, Et₂O, -5 deg C, 4 h

2: 70 percent / CF₃COOAg, NMM / tetrahydrofuran; H₂O / 8 h

With 4-methyl-morpholine; silver trifluoroacetate; isobutyl chloroformate; In tetrahydrofuran; water;

DOI:10.1002/hlca.19980810202

Reference yield:

Fmoc-Ser(tBu)-OH (71989-33-8) → Fmoc-β3-O-t-butyl-L-homoserine (203854-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 1H-benzotriazol-1-yl-N-oxytrispyrrolidinophosphonium PF₆^(1-); N-ethyldiisopropylamine / tetrahydrofuran; dimethylformamide; diethyl ether / 0.25 h / 0 °C

2: 74 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)-1-tert-Butoxymethyl-3-diazo-2-oxo-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Fmoc-Ser(tBu)-OH

Downstream raw materials:

H-(R)-β³hVal-(S)-β³hAla-(S)-β³hLys-(S)-β³hIle-(S)-β³hAla-(R)-β³hSer-(S)-β³hTyr-OH

Ac-(R)-β³hVal-(S)-β³hAla-(S)-β³hLys-(S)-β³hIle-(S)-β³hAla-(R)-β³hSer-(S)-β³hTyr-OH

Amino-PEG₆-(R)-β³hVal-(S)-β³hAla-(S)-β³hLys-(S)-β³hIle-(S)-β³hAla-(R)-β³hSer-(S)-β³hTyr-OH