Boc-Cys(Fm)-OH

Base Information

• Chemical Name: Boc-Cys(Fm)-OH
• CAS No.: 84888-35-7
• Molecular Formula: C22H25 N O4 S
• Molecular Weight: 399.511
• DSSTox Substance ID: DTXSID60427012
• Nikkaji Number: J282.294F
• Wikidata: Q72470135
• Mol file: 84888-35-7.mol

Synonyms:Boc-Cys(Fm)-OH;84888-35-7;Boc-S-Fluorenylmethyl-L-cysteine;(2R)-3-(9H-fluoren-9-ylmethylsulfanyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;SCHEMBL8541445;DTXSID60427012;AMY14559;MFCD00076921;AKOS015998819;L-Cysteine, N-[(1,1-dimethylethoxy)carbonyl]-S-(9H-fluoren-9-ylmethyl)-;AS-36990;CS-0208961;N-Boc-S-(9H-Fluoren-9-ylmethyl)-L-Cys-OH;N-[(1,1-Dimethylethoxy)carbonyl]-S-(9H-fluoren-9-ylmethyl)-L-cysteine;(R)-3-((9H-fluoren-9-yl)methylthio)-2-(tert-butoxycarbonylamino)propanoic acid;N-alpha-t-Butyloxycarbonyl-S-(9-fluorenylmethyl)-L-cysteine (Boc-L-Cys(Fm)-OH)

Chemical Property of Boc-Cys(Fm)-OH

Chemical Property:

• Vapor Pressure: 2.08E-15mmHg at 25°C
• Boiling Point: 603.4oC at 760 mmHg
• PKA: 3.54±0.10(Predicted)
• Flash Point: 318.7oC
• PSA: 100.93000
• Density: 1.237g/cm3
• LogP: 4.90090
• Storage Temp.: -15°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 399.15042945
• Heavy Atom Count: 28
• Complexity: 539

Purity/Quality:

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

Boc-S-9-fluorenylmethyl-L-cysteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CSCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CSCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)O

Technology Process of Boc-Cys(Fm)-OH

There total 7 articles about Boc-Cys(Fm)-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: 74.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-9H-fluorenyl-9-methyl-L-cysteine (84888-38-0,257288-48-5) → Nα-tert-butyloxycarbonyl-(S)-9-fluorenylmethylcysteine (84888-35-7)

Guidance literature:

With sodium carbonate; In water; tert-butyl alcohol; for 6h; pH 9-9.5;

DOI:10.1016/S0040-4020(01)81481-2

Reference yield: 60.0%

{[(tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile (80994-44-1) + S-Fm-L-cysteine (84888-34-6) → Nα-tert-butyloxycarbonyl-(S)-9-fluorenylmethylcysteine (84888-35-7)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; 1) 0 deg C, 15 min (pH 9.5) 2) 25 deg C, 2 h;

DOI:10.1055/s-1990-26804

Reference yield:

(9H-fluoren-9-yl)methyl 4-methylbenzenesulfonaye (71532-40-6) → Nα-tert-butyloxycarbonyl-(S)-9-fluorenylmethylcysteine (84888-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / N,N-diisopropylethylamine / dimethylformamide

2: 74 percent / 10percent Na₂CO₃ / 2-methyl-propan-2-ol; H₂O / 6 h / pH 9-9.5

With sodium carbonate; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)81481-2

upstream raw materials:

di-tert-butyl dicarbonate

(R)-9H-fluorenyl-9-methyl-L-cysteine

{[(tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile

S-Fm-L-cysteine

Downstream raw materials:

Boc-Ala-Ala-Thr-Cys-Phe-Ala-Arg-Asn-SH

L²,L-Ala_L⁵>enkephalinamide

L-cystine

Refernces

• 1、 Ponsati, Berta,Giralt, Ernest,Andreu, David. "Solid-phase approaches to regiospecific double disulfide formation. Application to a fragment of bovine pituitary peptide". . p. 8255 - 8266. Retrieved 2007/10/02.