Fmoc-D-Arg(Pmc)-OH

Base Information

• Chemical Name: Fmoc-D-Arg(Pmc)-OH
• CAS No.: 157774-30-6
• Molecular Formula: C₃₅H₄₂N₄O₇S
• Molecular Weight: 662.807
• DSSTox Substance ID: DTXSID30449908
• Mol file: 157774-30-6.mol

Synonyms:Fmoc-D-Arg(Pmc)-OH;157774-30-6;(2R)-5-[[amino-[(2,2,5,7,8-pentamethyl-3,4-dihydrochromen-6-yl)sulfonylamino]methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid;N-Alpha-Fmoc-N-g-(2,2,5,7,8-pentamethyl-chroman-6-sulfonyl)-D-arginine;SCHEMBL2366956;DTXSID30449908;AMY31369;MFCD00065619;AKOS015910376;Nalpha-Fmoc-Nomega-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-D-arginine;E70491;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(3-(2,2,5,7,8-pentamethylchroman-6-ylsulfonyl)guanidino)pentanoic acid;N-alpha-(9-Fluorenylmethoxycarbonyl)-N'-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-D-arginnine;N-alpha-(9-Fluorenylmethoxycarbonyl)-N'-(2,2,5,7,8pentamethylchroman-6-sulfonyl)-D-arginnine;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N'-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-D-arginine (Fmoc-D-Arg(Pmc)-OH);N2-(((9H-Fluoren-9-yl)methoxy)carbonyl)-Nw-((2,2,5,7,8-pentamethylchroman-6-yl)sulfonyl)-D-arginine

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

Chemical Property:

• PKA: 3.83±0.21(Predicted)
• PSA: 175.29000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 7.64340
• Storage Temp.: -15°C
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 662.27742087
• Heavy Atom Count: 47
• Complexity: 1230

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-D-Arg(Pmc)-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(CC2)(C)C)C)S(=O)(=O)NC(=NCCCC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)N)C
• Isomeric SMILES: CC1=C(C(=C(C2=C1OC(CC2)(C)C)C)S(=O)(=O)NC(=NCCC[C@H](C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)N)C

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

There total 9 articles about Fmoc-D-Arg(Pmc)-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: 89.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + NG-2,2,5,7,8-pentamethylchroman-6-sulfonyl-L-arginine (112160-37-9) → Fmoc-Arg(Pbf)-OH (119831-72-0,157774-30-6)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; for 1h;

DOI:10.1016/S0040-4020(01)86564-9

Reference yield:

2,2,5,7,8-pentamethyl-chromane (55646-01-0) → Fmoc-Arg(Pbf)-OH (119831-72-0,157774-30-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 53 percent / chlorosulphonic acid / CHCl₃ / 1.) -5 deg C, 15 min 2.) -5 deg C -> rt, 1 h

2: 3.2 M sodium hydroxide / acetone / 1.) 0 deg C, 2 h 2.) rt, 2 h

3: H₂ / 10percent Pd/C / methanol

4: 89 percent / 6percent aq. sodium carbonate / dimethylformamide / 1 h

With chlorosulfonic acid; sodium hydroxide; hydrogen; sodium carbonate; palladium on activated charcoal; In methanol; chloroform; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)86564-9

Reference yield:

2,3,5-trimethylphenol (697-82-5) → Fmoc-Arg(Pbf)-OH (119831-72-0,157774-30-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 44 percent / ZnCl₂ / acetic acid / 1.) 23 deg C, 12 h 2.) 150 deg C, 7 h

2: 53 percent / chlorosulphonic acid / CHCl₃ / 1.) -5 deg C, 15 min 2.) -5 deg C -> rt, 1 h

3: 3.2 M sodium hydroxide / acetone / 1.) 0 deg C, 2 h 2.) rt, 2 h

4: H₂ / 10percent Pd/C / methanol

5: 89 percent / 6percent aq. sodium carbonate / dimethylformamide / 1 h

With chlorosulfonic acid; sodium hydroxide; hydrogen; sodium carbonate; zinc(II) chloride; palladium on activated charcoal; In methanol; chloroform; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)86564-9

upstream raw materials:

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

N^G-2,2,5,7,8-pentamethylchroman-6-sulfonyl-L-arginine

(2R)-2-amino-5-{[(2,2,5,7,8-pentamethyl-3,4-dihydro-2H-chromen-6-yl)sulfonyl]carbamimidamido}pentanoic acid

2,2,5,7,8-pentamethyl-chromane

Downstream raw materials:

Tyr-Gly-Arg-Lys-Lys-Arg-Arg-Gln-Arg-Arg-Arg

C₄₆H₆₆N₈O₁₁S

C₄₅H₆₅N₇O₁₃S

[Sar¹,Val⁵]angiotensin II