tert-Butoxycarbonyl-L-valine N-hydroxysuccinimide ester

Base Information

• Chemical Name: tert-Butoxycarbonyl-L-valine N-hydroxysuccinimide ester
• CAS No.: 3392-12-9
• Molecular Formula: C14H22N2O6
• Molecular Weight: 314.338
• Hs Code.: 2925190090
• NSC Number: 164060
• Mol file: 3392-12-9.mol

Synonyms:Boc-Val-OSu;Carbamicacid, [(1S)-1-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]-2-methylpropyl]-, 1,1-dimethylethylester (9CI);Succinimide, N-[(N-carboxy-L-valyl)oxy]-,tert-butyl ester (7CI,8CI);Valine, N-carboxy-, N-tert-butyl ester, succinimidoderiv., L- (8CI);N-(tert-Butyloxycarbonyl)-L-valine ester with N-hydroxysuccinimide;N-tert-Butyloxycarbonyl-L-valine N-hydroxysuccinimide ester;NSC 164060;tert-Butoxycarbonyl-L-valine N-hydroxysuccinimide ester;tert-Butoxycarbonylvaline succinimide ester;

Chemical Property of tert-Butoxycarbonyl-L-valine N-hydroxysuccinimide ester

Chemical Property:

• Melting Point: 126-128 °C
• Refractive Index: 1.505
• PKA: 10.72±0.46(Predicted)
• PSA: 102.01000
• Density: 1.223 g/cm³
• LogP: 1.47170
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 314.14778643
• Heavy Atom Count: 22
• Complexity: 464

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-L-valine N-hydroxysuccinimide ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)ON1C(=O)CCC1=O)NC(=O)OC(C)(C)C

Technology Process of tert-Butoxycarbonyl-L-valine N-hydroxysuccinimide ester

There total 9 articles about tert-Butoxycarbonyl-L-valine N-hydroxysuccinimide 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%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + t-Boc-L-valine (13734-41-3) → Boc-Val-ONSu (3392-12-9)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 72h; Inert atmosphere; Sealed tube;

Reference yield: 99.0%

t-Boc-L-valine (13734-41-3) + Isopropenyl Succinimido Carbonate (96935-01-2) → Boc-Val-ONSu (3392-12-9)

Guidance literature:

With dmap; In 1,4-dioxane; for 4h; Ambient temperature;

DOI:10.1055/s-1991-26545

Reference yield: 92.0%

t-Boc-L-valine (13734-41-3) + 1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate (107960-02-1) → Boc-Val-ONSu (3392-12-9)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; acetonitrile; Ambient temperature;

DOI:10.1021/jo00388a005

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

t-Boc-L-valine

Isopropenyl Succinimido Carbonate

1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate

Downstream raw materials:

Val-Val

C₅₂H₇₈Cl₂N₈O₁₅

C₅₂H₇₆Cl₂N₈O₁₅

(3-{[(S)-3-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-1-(3,4-dichloro-benzyl)-2-oxo-imidazolidine-4-carbonyl]-amino}-2-hydroxy-hexanoylamino)-acetic acid allyl ester

Refernces

• 1、 Vatansever, Erol C.,Kang, Jeffrey,Tuley, Alfred,Ward, E. Sally,Liu, Wenshe Ray. "An optimal “Click” formulation strategy for antibody-drug conjugate synthesis". supporting information. . Retrieved 2020/10/20.
• 2、 Tereshchenkov, Andrey G.,Dobosz-Bartoszek, Malgorzata,Osterman, Ilya A.,Marks, James,Sergeeva, Vasilina A.,Kasatsky, Pavel,Komarova, Ekaterina S.,Stavrianidi, Andrey N.,Rodin, Igor A.,Konevega, Andrey L.,Sergiev, Petr V.,Sumbatyan, Natalia V.,Mankin, Alexander S.,Bogdanov, Alexey A.,Polikanov, Yury S.. "Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome". . p. 842 - 852. Retrieved 2018/02/26.