Fmoc-S-Methyl-L-Cysteine

Base Information

• Chemical Name: Fmoc-S-Methyl-L-Cysteine
• CAS No.: 138021-87-1
• Molecular Formula: C19H19 N O4 S
• Molecular Weight: 357.43
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID20427159
• Nikkaji Number: J1.464.405I
• Wikidata: Q72478633
• Mol file: 138021-87-1.mol

Synonyms:138021-87-1;FMOC-CYS(ME)-OH;Fmoc-S-Methyl-L-Cysteine;FMOC-S-METHYL-L-CYSETEINE;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(methylthio)propanoic acid;(2R)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-methylsulfanylpropanoic acid;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-S-methyl-L-cysteine;FMOC-L-CYS(ME)-OH;SCHEMBL3436129;DTXSID20427159;MFCD00237014;AKOS015837258;AKOS015907830;FD21305;HY-W048708;AS-49028;PD197196;CS-0101029;EN300-6737599;J-007087;N-(9H-Fluorene-9-ylmethoxycarbonyl)-S-methyl-L-cysteine;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-S-methyl-L-cysteine;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(methylsulfanyl)propanoic acid;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(methylthio)propanoic acid

Chemical Property of Fmoc-S-Methyl-L-Cysteine

Chemical Property:

• Boiling Point: 594.5±50.0 °C(Predicted)
• PKA: 3.40±0.10(Predicted)
• PSA: 100.93000
• Density: 1.308±0.06 g/cm3(Predicted)
• LogP: 3.73220
• Storage Temp.: 2-8°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 357.10347926
• Heavy Atom Count: 25
• Complexity: 464

Purity/Quality:

98%min ^*data from raw suppliers

Fmoc-S-methyl-L-cyseteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CSC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of Fmoc-S-Methyl-L-Cysteine

There total 2 articles about Fmoc-S-Methyl-L-Cysteine 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: 98.0%

S-methyl-L-cysteine (1187-84-4,7728-98-5) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-Fmoc-S-methyl-L-cysteine (138021-87-1)

Guidance literature:

DOI:10.1016/S0040-4039(99)01005-9

Reference yield:

→ N-Fmoc-S-methyl-L-cysteine (138021-87-1)

Guidance literature:

With trifluoroacetate; In dichloromethane; water;

DOI:10.1021/ol026947i

Reference yield: 91.0%

acetic anhydride (108-24-7) + N-Fmoc-S-methyl-L-cysteine (138021-87-1) → (2R)-2-acetylamino-3-methylthiopropionic acid (16637-59-5)

Guidance literature:

N-Fmoc-S-methyl-L-cysteine; chlorotrityl chloride (CTC) resin; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃;

With piperidine; In N,N-dimethyl-formamide; for 0.5h;

acetic anhydride;

DOI:10.1039/c7md00409e

upstream raw materials:

S-methyl-L-cysteine

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

(R)-4-methoxybenzyl-2-(((9-H-fluoren-9-yl)methoxy)carbonylamino)-3-(methylthio)propanoate

N-Fmoc-Cys(Me)-SPh

(9H-fluoren-9-yl)methyl vinylcarbamate

N-Fmoc-2-(methylthio)-1-(phenylthio)ethylamine

Refernces

• 1、 Matteucci, Mizio,Bhalay, Gurdip,Bradley, Mark. "Mild and highly chemoselective oxidation of thioethers mediated by Sc(OTf)3". . p. 235 - 237. Retrieved 2007/10/03.