Fmoc-Asp(OtBu)-OH

Base Information

• Chemical Name: Fmoc-Asp(OtBu)-OH
• CAS No.: 71989-14-5
• Molecular Formula: C23H25NO6
• Molecular Weight: 411.455
• Hs Code.: 29242990
• European Community (EC) Number: 276-251-7
• UNII: JHQ6MY724T
• DSSTox Substance ID: DTXSID001315581
• Nikkaji Number: J295.106A
• Wikidata: Q76145921
• ChEMBL ID: CHEMBL4633466
• Mol file: 71989-14-5.mol

Synonyms:Fmoc-Asp(OtBu)-OH;71989-14-5;Fmoc-L-Aspartic acid beta-tert-butyl ester;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid;Fmoc-Asp(OBut);Fmoc-L-Asp(OtBu)-OH;Fmoc-Asp(Ot-Bu)-OH;Fmoc-L-aspartic acid 4-tert-butyl ester;MFCD00037131;Fmoc-L-Asp(tBu);FmocAsp(OtBu)-OH;Fmoc-Asp(Obu)-OH;Fmoc-Asp(tBu)-OH;Fmoc-Asp(t-Bu)-OH;N-Alpha-Fmoc-L-aspartic acid beta-t-butyl ester;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid;4-(tert-butoxy)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-oxobutanoic acid;4-tert-Butyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-aspartate;FmocAsp(OBut)OH;N-alpha-FMOC-L-aspartic acid beta-tert-butyl ester;L-Fmoc-asparticacidalpha-t-butylester;Fmoc-L-aspartic acid beta-tert.buty ester;ST50307352;(2S)-4-(Tert-Butoxy)-2-{[(9H-Fluoren-9-Yl-Methoxy)Carbonyl]Amino}-4-Oxobutanoic Acid;JHQ6MY724T;SCHEMBL872021;CHEMBL4633466;4-tert-Butyl N-Fmoc-L-aspartate;FODJWPHPWBKDON-IBGZPJMESA-N;DTXSID001315581;BCP08108;CS-D1469;HY-Y1169;STL466193;AKOS015924105;AC-1156;(2S)-4-(tert-butoxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-oxobutanoic acid;(2S)-4-(tert-butoxy)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-oxobutanoic acid;L-aspartic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 4-(1,1-dimethylethyl) ester;Fmoc-3-(tert-Butoxycarbonyl)-L-Ala-OH;Fmoc-L-aspartic acid b-tert-butyl ester;AS-14174;BP-23513;BP-30008;N-Fmoc-L-aspartic Acid 4-tert-Butyl Ester;AM20060822;B3150;Fmoc-Asp(OtBu)-OH, >=98.0% (HPLC);EN300-96401;M03404;N-?-FMOC-L-aspartic acid ?-tert-butyl ester;A837378;J-300058;4-tert-Butyl N-(fluoren-9-ylmethoxycarbonyl)-L-aspartate;N-(Fluoren-9-ylmethoxycarbonyl)-L-aspartic acid 4-tert-butyl ester;N-9-Fluorenylmethyloxycarbonyl-L-aspartic acid beta-t-butyl ester;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-aspartic Acid 4-tert-Butyl Ester;(s)-2-(((9h-fluoren-9-yl)methoxy)carbonylamino)-4-tert-butoxy-4-oxobutanoic acid;(2S)-4-tert-butoxy-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-oxobutanoic acid (non-preferred name);N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-aspartic acid beta-t-butyl ester (Fmoc-L-Asp(OtBu)-OH)

Chemical Property of Fmoc-Asp(OtBu)-OH

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.83E-16mmHg at 25°C
• Melting Point: 148-150 °C (dec.)
• Refractive Index: -25 ° (C=1, DMF)
• Boiling Point: 620.8 °C at 760 mmHg
• PKA: 3.57±0.23(Predicted)
• Flash Point: 329.3 °C
• PSA: 101.93000
• Density: 1.251 g/cm³
• LogP: 4.10100
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 411.16818752
• Heavy Atom Count: 30
• Complexity: 620

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Fmoc-L-asparticAcidβ-tert-butylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)C[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: L-Aspartic acid is a nonessential amino acid that is used to biosynthesize other amino acids within the human body.

Technology Process of Fmoc-Asp(OtBu)-OH

There total 12 articles about Fmoc-Asp(OtBu)-OH 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: 78.0%

(9-fluorenyl)methyl pentafluorophenyl carbonate (88744-04-1) + L-Asp(t-Bu) (3057-74-7) → Fmoc-(tBu)Asp-OH (71989-14-5)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; Ambient temperature;

Reference yield: 68.0%

9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) + L-Asp(t-Bu) (3057-74-7) → Fmoc-(tBu)Asp-OH (71989-14-5)

Guidance literature:

With triethylamine; In water; acetonitrile; for 1h;

Reference yield: 64.0%

L-Asp(t-Bu) (3057-74-7) + Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester 9H-fluoren-9-ylmethyl ester (99503-04-5) → Fmoc-(tBu)Asp-OH (71989-14-5)

Guidance literature:

With tertiary amine; In 1,4-dioxane; water; for 3h;

DOI:10.1055/s-1987-27873

upstream raw materials:

9-fluorenylmethyl N-succinimidyl carbonate

L-Asp(t-Bu)

(9-fluorenyl)methyl pentafluorophenyl carbonate

Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester 9H-fluoren-9-ylmethyl ester

Downstream raw materials:

Fmoc-Asp(Ot-Bu)-ODbn

Fmoc-Asp(t-Bu)-Phe-NH₂

H-Tyr-Orn[*]-Phe-Asp[*]-NH₂

H-Tyr-D-Asp[*]-Phe-A₂bu[*]-NH₂

Refernces

• 1、 -. "Preparation method of N -fluorenylmethoxycarbonyl - L -aspartic -4 -tert-butyl ester". Paragraph 0027; 0034-0035; 0036; 0043-0044. . Retrieved 2021/08/25.
• 2、 Siciliano, Carlo,De Marco, Rosaria,Guidi, Ludovica Evelin,Spinella, Mariagiovanna,Liguori, Angelo. "A one-pot procedure for the preparation of N-9-fluorenylmethyloxycarbonyl- α-amino diazoketones from α-amino acids". . p. 10575 - 10582. Retrieved 2013/02/22.