Fmoc-D-beta-homoalanine

Base Information

• Chemical Name: Fmoc-D-beta-homoalanine
• CAS No.: 201864-71-3
• Molecular Formula: C19H19 N O4
• Molecular Weight: 325.364
• European Community (EC) Number: 816-480-7
• Nikkaji Number: J928.889I
• Wikidata: Q76148943
• Mol file: 201864-71-3.mol

Synonyms:Fmoc-D-beta-homoalanine;201864-71-3;Fmoc-D-3-Abu-OH;Butanoic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (3R)-;(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid;(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)butanoic acid;(3R)-3-[[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO]-BUTANOIC ACID;(3R)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid;Fmoc-3-D-aminobutanoic acid;(R)-3-(Fmoc-amino)butyric acid;MFCD00270344;Fmoc-?-HoAla-OH;Fmoc-D-Ala-(C#CH2)OH;SCHEMBL7391100;Fmoc--HoAla-OH Fmoc--homoalanine;Fmoc-D-b-Homoalanine, AldrichCPR;AKOS015900977;AC-22066;AS-31084;CS-0038508;EN300-624011;A879792;N-beta-(9-Fluorenylmethyloxycarbonyl)-D-homoalanine;Z2044821426;(3R)-3-(9H-Fluorene-9-ylmethoxycarbonylamino)butanoic acid;(3R)-3-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid;Butanoic acid,3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-,(3R)-

Chemical Property of Fmoc-D-beta-homoalanine

Chemical Property:

• Vapor Pressure: 3.64E-13mmHg at 25°C
• Melting Point: 97-99 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• Boiling Point: 555.3 ºC at 760 mmHg
• PKA: 4.38±0.10(Predicted)
• Flash Point: 289.6 ºC
• PSA: 75.63000
• Density: 1.255 g/cm³
• LogP: 3.77920
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly, Sonicated), DMF (Sparingly), DMSO (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 325.13140809
• Heavy Atom Count: 24
• Complexity: 444

Purity/Quality:

98% ^*data from raw suppliers

Fmoc-D-beta-homoalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Fmoc-D-beta-homoalanine

There total 4 articles about Fmoc-D-beta-homoalanine 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%

Fmoc-D-alanyl(diazo)methane (201864-69-9) → (R)-3-((fluorenylmethoxycarbonyl)amino)butyric acid (201864-71-3)

Guidance literature:

With silver benzoate; In 1,4-dioxane; water; at 70 ℃; for 5h;

Reference yield:

N-(9-fluorenylmethoxycarbonyl)-D-alanine (35661-38-2,35661-39-3,79990-15-1,136132-75-7) → (R)-3-((fluorenylmethoxycarbonyl)amino)butyric acid (201864-71-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Fmoc-Cl; N-methylmorpholine / tetrahydrofuran / 0.17 h / -15 °C

1.2: 86 percent / tetrahydrofuran; diethyl ether / 0 - 20 °C

2.1: 80 percent / silver benzoate / dioxane; H₂O / 0.02 h / microwave irradiation

With 4-methyl-morpholine; (fluorenylmethoxy)carbonyl chloride; silver benzoate; In tetrahydrofuran; 1,4-dioxane; water; 2.1: Wolff rearrangement;

Reference yield:

(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-propionic acid; hydrate (884880-37-9) → (R)-3-((fluorenylmethoxycarbonyl)amino)butyric acid (201864-71-3)

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: 73 percent / CF₃COOAg, Et₃N / tetrahydrofuran; H₂O

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

DOI:10.1002/hlca.19980810202

upstream raw materials:

Fmoc-D-alanyl(diazo)methane

N-(9-fluorenylmethoxycarbonyl)-D-alanine

(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-propionic acid; hydrate

Refernces

• 1、 Ananda,Suresh Babu. "Convenient and simple synthesis of N-{[(9H-fluoren-9- yl)methoxy]carbonyl}-(Fmoc) protected β-amino acids (=homo-α-amino acids) employing Fmoc-α-amino acids and dicyclohexylcarbodiimide(DCC) mixtures". . p. 418 - 423. Retrieved 2007/10/03.
• 2、 Ellmerer-Mueller, Ernst P.,Broessner, Dagmar,Maslouh, Najib,Tako, Andreas. "Synthesis of N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-Protected (Fmoc) β-Amino Acids (= Homo-α-Amino Acids) by Direct Homologation". . p. 59 - 65. Retrieved 2007/10/03.