Boc-Phe-OSu

Base Information

• Chemical Name: Boc-Phe-OSu
• CAS No.: 3674-06-4
• Molecular Formula: C18H22N2O6
• Molecular Weight: 362.382
• Hs Code.: 2925190090
• European Community (EC) Number: 222-939-7
• DSSTox Substance ID: DTXSID80190195
• Nikkaji Number: J26.003G
• Wikidata: Q72503980
• Mol file: 3674-06-4.mol

Synonyms:Boc-Phe-OSu;3674-06-4;Boc-L-phenylalanine N-hydroxysuccinimide ester;(2,5-dioxopyrrolidin-1-yl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate;MFCD00037911;(2,5-Dioxopyrrolidin-1-yl) (2S)-2-(tert-butoxycarbonylamino)-3-phenyl-propanoate;tert-Butyl (S)-(1-benzyl-2-((2,5-dioxo-1-pyrrolidinyl)oxy)-2-oxoethyl)carbamate;EINECS 222-939-7;BOC--Phe--OSu;2,5-dioxopyrrolidin-1-yl n-(tert-butoxycarbonyl)-l-phenylalaninate;N-Boc-Phe-(Succinimidyl)OH;SCHEMBL1032021;DTXSID80190195;BBL103719;STL557529;AKOS016842918;AM82169;CS-W009784;Boc-Phe-OSu, >=98.0% (HPLC);DS-16141;N-tert-butoxycarbonyl-L-phenylalanine succinimido ester;N-alpha-t-Butyloxycarbonyl-L-phenylalanine succinimidyl ester;2-(4-MORPHOLINYL)-PYRIDINE-4-CARBOXYLICACIDTERT-BUTYLESTER;(2,5-Dioxopyrrolidin-1-yl) (2S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoate;(S)-2,5-Dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate;(S)-2,5-dioxopyrrolidin-1-yl 2-(tert-butoxycarbonylamino)-3-phenylpropanoate

Chemical Property of Boc-Phe-OSu

Chemical Property:

• Melting Point: 150-152 °C
• Refractive Index: 1.561
• PKA: 10.76±0.46(Predicted)
• PSA: 102.01000
• Density: 1.281 g/cm³
• LogP: 2.05840
• Storage Temp.: −20°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 362.14778643
• Heavy Atom Count: 26
• Complexity: 547

Purity/Quality:

98%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(=O)ON2C(=O)CCC2=O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)ON2C(=O)CCC2=O
• Uses: (2,5-Dioxopyrrolidin-1-yl) (2S)-2-(tert-butoxycarbonylamino)-3-phenyl-propanoate is a useful research chemical.

Technology Process of Boc-Phe-OSu

There total 11 articles about Boc-Phe-OSu 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: 98.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → Boc-Phe-ONSu (3674-06-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In 1,2-dimethoxyethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1002/ejoc.201400154

Reference yield: 97.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + Isopropenyl Succinimido Carbonate (96935-01-2) → Boc-Phe-ONSu (3674-06-4)

Guidance literature:

With dmap; In 1,4-dioxane; at 20 ℃; for 19h;

DOI:10.1016/S0968-0896(03)00270-0

Reference yield: 92.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + bis(N-hydroxysuccinimide) sulfite (90704-86-2) → Boc-Phe-ONSu (3674-06-4)

Guidance literature:

With pyridine; In acetonitrile; at 20 ℃; for 1.5h; further solvent, base;

DOI:10.1007/BF01141728

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

N-tert-butoxycarbonyl-L-phenylalanine

Isopropenyl Succinimido Carbonate

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

Downstream raw materials:

Boc-L-Phe-L-Arg^NO₂-OMe

boc-Phe-Met-OH

Boc-Phe-Arg(NO₂)-OMe

(Z)-(S)-4-tert-Butoxycarbonylamino-2-cyano-3-hydroxy-5-phenyl-pent-2-enoic acid methyl ester

Refernces

• 1、 Karnthaler-Benbakka, Claudia,Koblmüller, Bettina,Mathuber, Marlene,Holste, Katharina,Berger, Walter,Heffeter, Petra,Kowol, Christian R.,Keppler, Bernhard K.. "Synthesis, Characterization and in vitro Studies of a Cathepsin B-Cleavable Prodrug of the VEGFR Inhibitor Sunitinib". . . Retrieved 2019/01/04.
• 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.