Fmoc-L-beta-glutamic acid 5-tert-butyl ester

Base Information

• Chemical Name: Fmoc-L-beta-glutamic acid 5-tert-butyl ester
• CAS No.: 209252-17-5
• Molecular Formula: C24H27NO6
• Molecular Weight: 425.47
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID80375809
• Nikkaji Number: J1.180.085H
• Wikidata: Q72478411
• Mol file: 209252-17-5.mol

Synonyms:209252-17-5;Fmoc-L-beta-glutamic acid 5-tert-butyl ester;Fmoc-|A-HoAsp(OtBu)-OH;Fmoc-beta-Glu(OtBu)-OH;Fmoc-beta-Hoasp(Otbu)-OH;(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid;(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid;Fmoc-L-beta-homoaspartic acid gamma-t-butyl ester;MFCD01862860;Fmoc-?-HoAsp(OtBu)-OH;SCHEMBL119715;Fmoc-I(2)-HoAsp(OtBu)-OH;Fmoc-Asp(OtBu)-(C#CH2)OH;fmoc-b-Homoaspartic acid (otbu);DTXSID80375809;AKOS016843062;Fmoc-L-beta-homoaspartic acid (OtBu);CS-W011640;DS-8540;HY-W010924;AM803497;Fmoc-beta-Glu(OtBu)-OH, >=95.0% (HPLC);(r)-3-(fmoc-amino)glutaric acid 1-tert-butyl ester;(3R)-5-tert-Butoxy-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-5-oxopentanoic acid;(R)-3-(9H-Fluorene-9-ylmethoxycarbonylamino)glutaric acid 1-tert-butyl ester

Chemical Property of Fmoc-L-beta-glutamic acid 5-tert-butyl ester

Chemical Property:

• Vapor Pressure: 4.22E-17mmHg at 25°C
• Melting Point: 82-83 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• Refractive Index: 1.57
• Boiling Point: 637 °C at 760 mmHg
• PKA: 4.24±0.10(Predicted)
• Flash Point: 339.1 °C
• PSA: 101.93000
• Density: 1.232 g/cm³
• LogP: 4.49110
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 425.18383758
• Heavy Atom Count: 31
• Complexity: 635

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-L-beta-glutamic acid 5-tert-butyl ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)C[C@@H](CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: N-Fmoc-L-beta-glutamic acid 5-tert-butyl ester, is a protected building block used for the introduction of glutamic acid into peptides. Fmoc-beta-Glu(OtBu)-OH) was hydrolyzed with trifluoroacetic acid (TFA) and isolated with the HPLC system to give Fmoc-beta-Glu(OH)-OH.

Technology Process of Fmoc-L-beta-glutamic acid 5-tert-butyl ester

There total 7 articles about Fmoc-L-beta-glutamic acid 5-tert-butyl ester 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: 80.0%

tert-butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-diazo-4-oxopentanoate (244031-63-8) → (9H-fluoren-9-yl)methyl (R)-1-(hydroxycarbonyl)-3-(tert-butoxycarbonyl)propan-2-ylcarbamate (209252-17-5,1246651-90-0)

Guidance literature:

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

Reference yield:

Fmoc-(tBu)Asp-OH (71989-14-5) → (9H-fluoren-9-yl)methyl (R)-1-(hydroxycarbonyl)-3-(tert-butoxycarbonyl)propan-2-ylcarbamate (209252-17-5,1246651-90-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 1H-benzotriazol-1-yl-N-oxytrispyrrolidinophosphonium PF₆^(1-); N-ethyldiisopropylamine / tetrahydrofuran; dimethylformamide; diethyl ether / 0.25 h / 0 °C

2: 79 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;

Reference yield:

Fmoc-Asp(OtBu)-OCO2i-Bu → (9H-fluoren-9-yl)methyl (R)-1-(hydroxycarbonyl)-3-(tert-butoxycarbonyl)propan-2-ylcarbamate (209252-17-5,1246651-90-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran

2: Et₃N / Ag benzoate / dioxane; H₂O

With triethylamine; silver benzoate; In tetrahydrofuran; 1,4-dioxane; water; 1: Arndt-Eistert reaction / 2: Wolf rearrangement;

DOI:10.1016/S0040-4039(03)01471-0

upstream raw materials:

tert-butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-diazo-4-oxopentanoate

Fmoc-(tBu)Asp-OH

Downstream raw materials:

C₃₂H₃₅N₃O₆

(1,1-dimethylethyl-3-(R)-[[9H-fluoren-9-ylmethoxy)carbonyl]-amino]-4-[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]butanoate

3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(3-p-tolyl-[1,2,4]oxadiazol-5-yl)-butyric acid allyl ester

C₃₁H₃₁N₃O₆