Fmoc-D-Arg(NO2)-OH

Base Information

• Chemical Name: Fmoc-D-Arg(NO2)-OH
• CAS No.: 160347-94-4
• Molecular Formula: C₂₁H₂₃N₅O₆
• Molecular Weight: 441.444
• DSSTox Substance ID: DTXSID90579952
• Mol file: 160347-94-4.mol

Synonyms:Fmoc-D-Arg(NO2)-OH;160347-94-4;fmoc-nw-nitro-d-arginine;(2R)-5-[[amino(nitramido)methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-(N'-nitrocarbamimidamido)pentanoic acid;D-Ornithine, N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-N5-[imino(nitroamino)methyl]-;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(3-nitroguanidino)pentanoic acid;Fmoc-Nw-nitro-L-arginine;FMOC-N-OMEGA-NITRO-D-ARGININE;DTXSID90579952;AMY22777;MFCD02682438;AKOS016842955;AS-73746;D86867;EN300-7370059;N2-(((9H-Fluoren-9-yl)methoxy)carbonyl)-Nw-nitro-D-arginine;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(3-nitroguanidino)pentanoicacid;(E)-N~5~-[Amino(nitroamino)methylidene]-N~2~-{[(9H-fluoren-9-yl)methoxy]carbonyl}-D-ornithine

Chemical Property of Fmoc-D-Arg(NO2)-OH

Chemical Property:

• Storage Temp.: Store at?0-5°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 441.16483347
• Heavy Atom Count: 32
• Complexity: 689

Purity/Quality:

98%min ^*data from raw suppliers

Fmoc-D-Arg(NO2)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCCN=C(N)N[N+](=O)[O-])C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CCCN=C(N)N[N+](=O)[O-])C(=O)O

Technology Process of Fmoc-D-Arg(NO2)-OH

There total 2 articles about Fmoc-D-Arg(NO2)-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: 73.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + Nω-nitro-D-arginine (66036-77-9,13855-78-2,38733-00-5) → Fmoc-D-Arg(NO2)-OH (160347-94-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 15h;

DOI:10.1021/ja0666250

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + Nω-nitro-D-arginine (66036-77-9,13855-78-2,38733-00-5) → Fmoc-D-Arg(NO2)-OH (160347-94-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane;

DOI:10.1016/j.tetlet.2006.03.190

Reference yield: 92.0%

L-phenylalanine tert-butyl ester (16874-17-2) + Fmoc-D-Arg(NO2)-OH (160347-94-4) → H-D-Arg(NO2)-L-Phe tert-butyl ester

Guidance literature:

L-phenylalanine tert-butyl ester; Fmoc-D-Arg(NO₂)-OH; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/anie.201803549

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

Nω-nitro-D-arginine

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Refernces

• 1、 Krishnamoorthy, Ravi,Vazquez-Serrano, Leslie D.,Turk, Jeffrey A.,Kowalski, Jennifer A.,Benson, Alan G.,Breaux, Nneka T.,Lipton, Mark A.. "Solid-phase total synthesis and structure proof of callipeltin B". . p. 15392 - 15393. Retrieved 2007/10/03.