Boc-D-Arg(Pbf)-OH

Base Information

• Chemical Name: Boc-D-Arg(Pbf)-OH
• CAS No.: 186698-61-3
• Molecular Formula: C₂₄H₃₈N₄O₇S
• Molecular Weight: 526.654
• DSSTox Substance ID: DTXSID10583793
• Mol file: 186698-61-3.mol

Synonyms:Boc-D-Arg(Pbf)-OH;186698-61-3;(2R)-5-[[amino-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;MFCD00236822;Boc-Nw-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-D-arginine;DEMECARIUMBROMIDE(250MG);DTXSID10583793;CVFXPOKENLGCID-QGZVFWFLSA-N;AKOS025289352;DS-9740;HY-W062304;CS-0054158;I10279;A854683;(E)-N~5~-{Amino[(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)amino]methylidene}-N~2~-(tert-butoxycarbonyl)-D-ornithine;D-Ornithine,N5-[[[(2,3-dihydro-2,2,4,6,7-pentamethyl-5-benzofuranyl)sulfonyl]amino]iminomethyl]-N2-[(1,1-dimethylethoxy)carbonyl]-;N-alpha-(t-Butyloxycarbonyl)-N'-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-D-arginine;N2-(tert-Butoxycarbonyl)-Nw-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)-D-arginine

Chemical Property of Boc-D-Arg(Pbf)-OH

Chemical Property:

• PKA: 3.94±0.21(Predicted)
• PSA: 175.29000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 5.23930
• Storage Temp.: -15°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 526.24612074
• Heavy Atom Count: 36
• Complexity: 939

Purity/Quality:

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

Boc-D-Arg(Pbf)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=C(C2=C1OC(C2)(C)C)C)S(=O)(=O)NC(=NCCCC(C(=O)O)NC(=O)OC(C)(C)C)N)C
• Isomeric SMILES: CC1=C(C(=C(C2=C1OC(C2)(C)C)C)S(=O)(=O)NC(=NCCC[C@H](C(=O)O)NC(=O)OC(C)(C)C)N)C

Technology Process of Boc-D-Arg(Pbf)-OH

There total 2 articles about Boc-D-Arg(Pbf)-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: 82.0%

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8,113712-06-4) + 2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonyl chloride (154445-78-0) → (S)-2-(tert-butoxycarbonylamino)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanoic acid (186698-61-3)

Guidance literature:

With sodium hydroxide; In water; acetone; at 5 ℃; for 1h; Temperature;

Reference yield:

Fmoc-Arg(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-OMe → (S)-2-(tert-butoxycarbonylamino)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanoic acid (186698-61-3)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.24820/ARK.5550190.P011.484

Reference yield: 76.0%

(S)-2-(tert-butoxycarbonylamino)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanoic acid (186698-61-3) + celecoxib sodium salt → C41H50F3N7O8S2 (1538609-34-5)

Guidance literature:

(S)-2-(tert-butoxycarbonylamino)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanoic acid; celecoxib sodium salt; With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In dichloromethane; at 25 ℃; for 0.75h;

With triethylamine; In dichloromethane; at 25 ℃; for 52h;

upstream raw materials:

N^α-t-butoxycarbonyl-arginine hydrochloride

2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonyl chloride

Downstream raw materials:

(S)-N¹-((S)-1,5-diamino-1-imino-6,15-dioxo-2,7,12,16-tetraazahenicosan-21-yl)-2-(2-(2,4-dihydroxyphenyl)acetamido)-succinamide tris(2,2,2-trifluoroacetate)

C₄₁H₅₀F₃N₇O₈S₂

Refernces

• 1、 -. "Synthetic method for N-t-butyloxycarboryl-N'-(pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine". Paragraph 0005; 0008-0016. . Retrieved 2018/12/14.