2-Tert-butoxycarbonylamino-pentanedioic acid 1-tert-butyl ester

Base Information

• Chemical Name: 2-Tert-butoxycarbonylamino-pentanedioic acid 1-tert-butyl ester
• CAS No.: 24277-39-2
• Molecular Formula: C14H25NO6
• Molecular Weight: 303.356
• Hs Code.: 2924 19 00
• NSC Number: 164659
• Nikkaji Number: J2.218.474A
• Mol file: 24277-39-2.mol

Synonyms:2-tert-butoxycarbonylamino-pentanedioic acid 1-tert-butyl ester;5-[(2-methylpropan-2-yl)oxy]-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid;Boc-L-Glutamic acid alpha-t-butyl ester;MFCD00038273;MFCD00076926;N-Boc-L-glutamic Acid tert-Butyl Ester;NSC164659;N-Boc-D-glutamic acid 1-(tert-butyl) ester;SCHEMBL863895;YMOYURYWGUWMFM-UHFFFAOYSA-N;AKOS024319049;NSC-164659;AS-17495;SY030364;SY034168;Boc-D-glutamic acid alfa-tert-butyl ester;Boc-L-glutamic acid alpha-tert.butyl ester;AM20090268;FT-0629761;FT-0629762;FT-0688453;Glutamic acid, N,1-di-tert-butyl ester, L-;L-Glutamic acid,1-dimethylethoxy)carbonyl]-, 1-(1,1-dimethylethyl) ester

Chemical Property of 2-Tert-butoxycarbonylamino-pentanedioic acid 1-tert-butyl ester

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.42E-09mmHg at 25°C
• Melting Point: 111.0 to 115.0 °C
• Refractive Index: 1.47
• Boiling Point: 449.8 °C at 760 mmHg
• PKA: 4.48±0.10(Predicted)
• Flash Point: 225.8 °C
• PSA: 101.93000
• Density: 1.121 g/cm³
• LogP: 2.47710
• Storage Temp.: −20°C
• Solubility.: Soluble in dimethyl formamide.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 303.16818752
• Heavy Atom Count: 21
• Complexity: 391

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-glutamic acid a-t-butyl ester ^*data from reagent suppliers

Safty Information:

• Statements: 22/22-36/37/38
• Safety Statements: 4-7-28-35-44

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CCC(=O)O)NC(=O)OC(C)(C)C
• Uses: Boc-Glu-OtBu is an N-terminal protected amino acid used in solid-phase peptide synthesis (SPPS) to make unique peptides containing glutamate tert-butyl ester residues.

Technology Process of 2-Tert-butoxycarbonylamino-pentanedioic acid 1-tert-butyl ester

There total 29 articles about 2-Tert-butoxycarbonylamino-pentanedioic acid 1-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: 100.0%

N-tert-butoxyxarbonyl-L-glutamic acid γ-benzyl α-tert-butyl diester (28812-54-6) → N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1039/a806741d

Reference yield: 96.0%

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate (91229-91-3) → N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1039/b503900b

Reference yield: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + N-(diphenylmethylene)-L-glutamic acid 1-(1,1-dimethylethyl) 5-benzyl ester (611182-62-8) → N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2)

Guidance literature:

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; for 20h;

DOI:10.1021/ja037290e

upstream raw materials:

(S)-(-)-1-tert-butyl-5-methyl-<(2-tert-butoxycarbonyl)amino>pentanedioate

N-tert-butoxyxarbonyl-L-glutamic acid γ-benzyl α-tert-butyl diester

di-tert-butyl dicarbonate

N-(diphenylmethylene)-L-glutamic acid 1-(1,1-dimethylethyl) 5-benzyl ester

Downstream raw materials:

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

N-(4-methoxyphenyl)methyl-N²-(t-butoxycarbonyl)-L-glutamine 1-t-butyl ester

1,3-Dicyclohexylurea

4-(2-hydroxyethylthioethyl)-L-glutamate

Refernces

Expedient synthesis of a novel class of pseudoaromatic amino acids: Tetrahydroindazol-3-yl- and tetrahydrobenzisoxazol-3-ylalanine derivatives

10.1016/j.tetlet.2003.11.133

The study presents a concise synthesis method for a novel class of homochiral aromatic amino acid surrogates, featuring tetrahydroindazole or benzisoxazole systems. These surrogates were synthesized through the acylation of cyclic 1,3-diketone by the side-chain carboxyl functionality of specific amino acid precursors, followed by a regioselective condensation with hydrazine, N-benzylhydrazine, and hydroxylamine. The synthetic strategy is versatile, allowing for the creation of structurally diverse derivatives. These novel amino acids can be efficiently incorporated into proteins and have potential applications in imparting unique properties to biological peptides. The study also includes the synthesis of Na-Fmoc-protected derivatives, which are useful for solid-phase peptide assembly, and the exploration of the stereochemistry integrity of the homochiral starting material through chemical transformations. The synthesized amino acids offer opportunities as structural surrogates of tryptophan and as building blocks for designing molecular probes.