Fmoc-D-Glu(OtBu)-OH

Base Information

• Chemical Name: Fmoc-D-Glu(OtBu)-OH
• CAS No.: 104091-08-9
• Molecular Formula: C24H27NO6
• Molecular Weight: 425.481
• Hs Code.: 2924 29 70
• European Community (EC) Number: 860-518-5
• DSSTox Substance ID: DTXSID60427037
• Wikidata: Q72478417
• Mol file: 104091-08-9.mol

Synonyms:Fmoc-D-Glu(OtBu)-OH;104091-08-9;Fmoc-D-glutamic acid 5-tert-butyl ester;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid;MFCD00077055;Fmoc-D-glutamic acid gamma-tert-butyl ester;Fmoc-D-Glu(OtBu)-OH H;SCHEMBL120511;Fmoc-D-Glu(OtBu)-OH.nH2O;DTXSID60427037;Fmoc-D-Glu(OtBu)-OH,Nonhydrate;5-tert-Butyl N-Fmoc-D-glutamate;OTKXCALUHMPIGM-HXUWFJFHSA-N;AMY17975;HY-Y1844;AKOS015924150;AC-8592;CS-W020643;FD21434;D-Glutamic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-,5-(1,1-dimethylethyl) ester;AC-28370;AS-12875;B3669;EN300-316692;Fmoc-D-Glu(OtBu)-OH, >=98.0% (HPLC);M03413;A800893;FMOC-D-GLUTAMIC ACID GAMMA-TERT-BUTYLESTER;5-tert-Butyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-glutamate;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-glutamic Acid 5-tert-Butyl Ester;(2R)-5-(tert-butoxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-oxopentanoic acid;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-tert-butoxy-5-oxopentanoic acid;2-tert-butyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)pentanedioic acid

Chemical Property of Fmoc-D-Glu(OtBu)-OH

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 6.39E-17mmHg at 25°C
• Melting Point: 83-89 °C
• Refractive Index: 1.57
• Boiling Point: 633.5 °C at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 336.9 °C
• PSA: 101.93000
• Density: 1.232 g/cm³
• LogP: 4.49110
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 3.9
• 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:

99% ^*data from raw suppliers

Fmoc-D-Glu(OtBu)-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)CC[C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: It is an important raw material and intermediate used in organic synthesis, agrochemicals and dyestuff.

Technology Process of Fmoc-D-Glu(OtBu)-OH

There total 5 articles about Fmoc-D-Glu(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: 100.0%

N-Fmoc-D-Glu α-benzyl, γ-tert-butyl ester (104091-07-8) → Fmoc-Glu(OtBu)-OH (104091-08-9)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In tetrahydrofuran; methanol; at 0 - 5 ℃; for 0.333333h;

DOI:10.1021/jo00374a019

Reference yield: 70.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (R)-2-amino-5-(tert-butoxy)-5-oxopentanoic acid (45125-00-6) → Fmoc-Glu(OtBu)-OH (104091-08-9)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; 1.) 0 deg C, 2 h, 2.) 25 deg C, 18 h;

DOI:10.1021/jo00374a019

Reference yield:

N-Fmoc-D-glutamic acid (104091-09-0) → Fmoc-Glu(OtBu)-OH (104091-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) N,N'dicyclohexylcarbodiimide, 2.) potassium carbonate / 1.) THF, 23 h, 2.) THF, 3.5 h

2: 85 percent / sulfur acid / CH₂Cl₂ / 6 h / 25 °C / 1499.7 Torr

3: 100 percent / ammonium formate / 10percent Pd/C / methanol; tetrahydrofuran / 0.33 h / 0 - 5 °C

With sulfuric acid; ammonium formate; potassium carbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00374a019

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(R)-2-amino-5-(tert-butoxy)-5-oxopentanoic acid

N-Fmoc-D-Glu α-benzyl, γ-tert-butyl ester

N-Fmoc-D-glutamic acid

Downstream raw materials:

N-Fmoc-D-glutamic acid

Fmoc-D-Glu(OH)-NH-paratolyl

(R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid

4-(2-acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-[1-(1-{2-cyclohexyl-1-[1-ethyl-4-(4-methoxy-phenyl)-2-oxo-butylcarbamoyl]-ethylcarbamoyl}-2-methyl-butylcarbamoyl)-3-methyl-butylcarbamoyl]-butyric acid tert-butyl ester

Refernces

• 1、 Kelly, Robert C.,Gebhard, I.,Wicnienski, N.. "Synthesis of (R)- and (S)-(glu)Thz and the Corresponding Bisthiazole Dipeptide of Dolastatin 3". . p. 4590 - 4594. Retrieved 2007/10/02.