FMOC-ARG(BOC)2-OH

Base Information

• Chemical Name: FMOC-ARG(BOC)2-OH
• CAS No.: 143824-77-5
• Molecular Formula: C31H40 N4 O8
• Molecular Weight: 596.681
• Hs Code.: 2934999090
• Mol file: 143824-77-5.mol

Synonyms:L-Ornithine,N5-[bis[[(1,1-dimethylethoxy)carbonyl]amino]methylene]-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-;11-Oxa-2,7,9-triazatridec-7-enoic acid,3-carboxy-8-[[(1,1-dimethylethoxy)carbonyl]amino]-12,12-dimethyl-10-oxo-,1-(9H-fluoren-9-ylmethyl) ester, (S)-

Chemical Property of FMOC-ARG(BOC)2-OH

Chemical Property:

• PKA: 3.80±0.21(Predicted)
• PSA: 167.35000
• Density: 1.255g/cm3
• LogP: 6.33660
• Storage Temp.: -15°C

Purity/Quality:

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

Fmoc-Arg(Boc)2-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Fmoc-Arg(Boc)2-OH is an intermediate used in membrane enhanced peptide synthesis.

Technology Process of FMOC-ARG(BOC)2-OH

There total 12 articles about FMOC-ARG(BOC)2-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: 99.6%

9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) + H-Argω,ω'(Boc)2-OH (145315-38-4) → Fmoc-Argω,ω'(Boc)2-OH (143824-77-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1.16667h;

DOI:10.1016/S0040-4039(00)79037-X

Reference yield: 84.0%

9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) + H-L-Arg(Boc)2-OH (145315-38-4) → N-α-(9-fluorenylmethyloxycarbonyl)-N-ω′,N-ω″-bis-tert-butyloxycarbonyl-L-argine (143824-77-5)

Guidance literature:

With ethylenediaminetetraacetic acid; sodium hydrogencarbonate; In acetone; at 20 ℃;

DOI:10.1016/j.bmcl.2003.12.030

Reference yield:

Nα-benzyloxycarbonyl-L-ornithine (2640-58-6) → Fmoc-Argω,ω'(Boc)2-OH (143824-77-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Triton-B / methanol; dimethylsulfoxide / 40 h / 10 °C

2: 99 percent / hydrogen / 10percent Pd/C / methanol / 0.67 h / 1551.4 Torr

3: 99.6 percent / DIPEA / CH₂Cl₂ / 1.17 h

With hydrogen; N-benzyl-trimethylammonium hydroxide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)79037-X

upstream raw materials:

9-fluorenylmethyl N-succinimidyl carbonate

H-Arg^ω,ω'(Boc)2-OH

Nα-benzyloxycarbonyl-L-ornithine

1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea

Refernces

• 1、 Zhu, Ruixin,Xie, Ming,Wang, Fei,Liu, Qi,Kang, Tingguo. "An efficient and economical method for the preparation of Fmoc-Arg ωω (Boc) 2-OH". experimental part. p. 1508 - 1509. Retrieved 2011/01/04.
• 2、 Feichtinger, Konrad,Zapf, Christoph,Sings, Heather L.,Goodman, Murray. "Diprotected Triflylguanidines: A New Class of Guanidinylation Reagents". . p. 3804 - 3805. Retrieved 2007/10/03.