Fmoc-D-Orn(Boc)-OH

Base Information

• Chemical Name: Fmoc-D-Orn(Boc)-OH
• CAS No.: 118476-89-4
• Molecular Formula: C₂₅H₃₀N₂O₆
• Molecular Weight: 454.523
• Hs Code.: 2924 29 70
• European Community (EC) Number: 806-364-4
• DSSTox Substance ID: DTXSID40553924
• Wikidata: Q72478143
• Mol file: 118476-89-4.mol

Synonyms:Fmoc-D-Orn(Boc)-OH;118476-89-4;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;N-Fmoc-N'-Boc-D-ornithine;Fmoc-(Nd-Boc)-D-ornithine;(2R)-5-{[(tert-butoxy)carbonyl]amino}-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pentanoic acid;MFCD00077065;JOOIZTMAHNLNHE-OAQYLSRUSA-N;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoic acid;SCHEMBL1637300;DTXSID40553924;fmoc-D-orn(boc)-oh, AldrichCPR;AMY22566;N-alpha-Fmoc-N-D-t-boc-D-ornithine;AKOS005145753;CS-W007114;N-|A-Fmoc-N-|A-t.-Boc-D-ornithine;AS-56978;EN300-317232;(R)-N5 -(tert.-butoxy-carbonyl)-N2 -(9-fluorenylmethoxycarbonyl)-ornithine;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(tert-butoxycarbonylamino)pentanoic acid;(R)-5-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid;5-t-butoxycarbonylamino-(2R)-(9H-fluoren-9-ylmethoxycarbonyl amino)-pentanoic acid;5-t-butoxycarbonylamino-(2R)-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid;N~5~-(tert-Butoxycarbonyl)-N~2~-{[(9H-fluoren-9-yl)methoxy]carbonyl}-D-ornithine;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-delta-(t-butyloxycarbonyl)-D-ornithine (Fmoc-D-Orn(Boc)-OH)

Chemical Property of Fmoc-D-Orn(Boc)-OH

Chemical Property:

• Vapor Pressure: 2.28E-19mmHg at 25°C
• Refractive Index: 1.57
• Boiling Point: 679.036 °C at 760 mmHg
• PKA: 3.85±0.21(Predicted)
• Flash Point: 364.468 °C
• PSA: 113.96000
• Density: 1.226 g/cm³
• LogP: 5.06500
• Storage Temp.: Store at RT.
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 454.21038668
• Heavy Atom Count: 33
• Complexity: 669

Purity/Quality:

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

Fmoc-D-Orn(Boc)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)NCCC[C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-D-Orn(Boc)-OH is a reagent used for the synthesis of bisquinoline analogs with antileishmanial and antimicrobial activities against a panel of pathogenic bacteria and fungi.

Technology Process of Fmoc-D-Orn(Boc)-OH

There total 10 articles about Fmoc-D-Orn(Boc)-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: 94.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + copper(II) complex of Nδ-tert-butoxycarbonyl-L-ornithine → Fmoc-Orn(Boc)-OH (109425-55-0,118476-89-4)

Guidance literature:

copper(II) complex of N^δ-tert-butoxycarbonyl-L-ornithine; With 8-quinolinol; sodium carbonate; In acetone; for 1h;

(fluorenylmethoxy)carbonyl chloride; With 1-hydroxy-pyrrolidine-2,5-dione; In water; at -5 ℃; for 0.5h;

DOI:10.1248/cpb.49.1189

Reference yield: 93.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + Nδ-(tert-butoxycarbonyl)-L-ornithine (13650-49-2,184576-63-4) → Fmoc-Orn(Boc)-OH (109425-55-0,118476-89-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1002/psc.2968

Reference yield: 83.0%

Fmoc-Orn(Boc)-1,1-dimethylallyl ester (851713-95-6) → Fmoc-Orn(Boc)-OH (109425-55-0,118476-89-4)

Guidance literature:

With 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/ol0476117

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

di-tert-butyl dicarbonate

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

L-ornithine hydrochloride

Downstream raw materials:

H-Tyr-Orn[*]-Phe-Asp[*]-NH₂

H-Tyr-D-Orn[*]-Phe-D-Asp[*]-NH₂

H-Tyr-D-Orn[*]-D-Phe-Asp[*]-NH₂

H-Tyr-D-Orn[*]-Phe(NMe)-Asp[*]-NH₂

Refernces

• 1、 Pícha, Jan,Budě?ínsky, Milo?,Machá?ková, Kate?ina,Collinsová, Michaela,Jirá?ek, Ji?í. "Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides". . p. 202 - 214. Retrieved 2017/04/06.
• 2、 Zhao, Yinan,Zhang, Shubiao,Zhang, Yuan,Cui, Shaohui,Chen, Huiying,Zhi, Defu,Zhen, Yuhong,Zhang, Shufen,Huang, Leaf. "Tri-peptide cationic lipids for gene delivery". . p. 119 - 126. Retrieved 2015/02/19.