Fmoc-Cys(4-MeBzl)-OH

Base Information

• Chemical Name: Fmoc-Cys(4-MeBzl)-OH
• CAS No.: 136050-67-4
• Molecular Formula: C26H25 N O4 S
• Molecular Weight: 447.55
• DSSTox Substance ID: DTXSID30583811
• Wikidata: Q72478624
• Mol file: 136050-67-4.mol

Synonyms:136050-67-4;Fmoc-Cys(4-MeBzl)-OH;Fmoc-Cys(Mbzl)-OH;FMOC-CYS(4-MBZL)-OH;Fmoc-S-(4-methylbenzyl)-L-cysteine;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methylphenyl)methylsulfanyl]propanoic acid;N-Fmoc-S-(4-methylbenzyl)-L-cysteine;MFCD00065634;Fmoc-Cys(CH3Bzl)-OH;SCHEMBL16634948;DTXSID30583811;AKOS015837243;AKOS015897322;AC-8588;CS-W011587;FD21301;HY-W010871;DS-16151;J-006797;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-S-(4-methylbenzyl)-L-cysteine;N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-S-[(4-methylphenyl)methyl]-L-cysteine;N-alpha-(9-Fluorenylmethyloxycarbonyl)-S-(4-methylbenZyl)-L-cysteine (Fmoc-L-Cys(MBZl)-OH)

Chemical Property of Fmoc-Cys(4-MeBzl)-OH

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 5.87E-19mmHg at 25°C
• Melting Point: 150-158 °C
• Boiling Point: 671.7oC at 760 mmHg
• PKA: 3.46±0.10(Predicted)
• Flash Point: 360oC
• PSA: 100.93000
• Density: 1.278g/cm3
• LogP: 5.61100
• Storage Temp.: 2-8°C
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 447.15042945
• Heavy Atom Count: 32
• Complexity: 613

Purity/Quality:

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

Fmoc-Cys(4-mbzl)-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)CSCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: CC1=CC=C(C=C1)CSC[C@@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of Fmoc-Cys(4-MeBzl)-OH

There total 4 articles about Fmoc-Cys(4-MeBzl)-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: 70.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + S-<(4-methylphenyl)methyl>-L-cysteine (42294-52-0) → Nα-Fmoc-S-(4-methylbenzyl)cysteine (136050-67-4)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; for 3h;

Reference yield:

N,N'-bis[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cystine (135273-01-7) → Nα-Fmoc-S-(4-methylbenzyl)cysteine (136050-67-4)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc; hydrogenchloride / water; ethyl acetate

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; zinc; In dichloromethane; water; ethyl acetate;

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Nα-Fmoc-S-(4-methylbenzyl)cysteine (136050-67-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium carbonate / acetone; water / 50 °C

2: zinc; hydrogenchloride / water; ethyl acetate

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h

With hydrogenchloride; sodium carbonate; N-ethyl-N,N-diisopropylamine; zinc; In dichloromethane; water; ethyl acetate; acetone;

upstream raw materials:

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

S-<(4-methylphenyl)methyl>-L-cysteine

N^α-fluoren-9-ylmethoxycarbonyl-L-cysteine

4-Methylbenzyl bromide

Downstream raw materials:

N^α-Fmoc-α-benzyl-γ-glutamyl--β-alanine ethyl ester

3-[(R)-2-Amino-3-(4-methyl-benzylsulfanyl)-propionylamino]-propionic acid ethyl ester

Refernces

• 1、 Lyttle,Hocker,Hui,Caldwell,Aaron,Engqvist- Goldstein,Flatgaard,Bauer. "Isozyme-specific glutathione-S-transferase inhibitors: Design and synthesis". . p. 189 - 194. Retrieved 2007/10/02.