Boc-L-cysteine

Base Information

• Chemical Name: Boc-L-cysteine
• CAS No.: 20887-95-0
• Molecular Formula: C8H15NO4S
• Molecular Weight: 221.277
• Hs Code.: 29309090
• DSSTox Substance ID: DTXSID30175033
• Nikkaji Number: J272.622J
• Wikidata: Q72449070
• Mol file: 20887-95-0.mol

Synonyms:Boc-L-cysteine;N-tert-butyloxycarbonylcysteine

Chemical Property of Boc-L-cysteine

Chemical Property:

• Appearance/Colour: light yellow liquid
• Vapor Pressure: 3.34E-06mmHg at 25°C
• Melting Point: 67-70 °C
• Refractive Index: 1.503
• Boiling Point: 361.4 °C at 760 mmHg
• PKA: 3.57±0.10(Predicted)
• Flash Point: 172.3 °C
• PSA: 114.43000
• Density: 1.215 g/cm³
• LogP: 1.28500
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 221.07217913
• Heavy Atom Count: 14
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-cysteine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CS)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CS)C(=O)O
• Uses: Boc-L-cysteine is the protected form of L-Cysteine (C995000), a non-essential α-amino acid that is biosynthesized in humans. L-Cysteine is also a bicarbonate-sensitive endogenous excitotoxin in rats and possibly humans.

Technology Process of Boc-L-cysteine

There total 3 articles about Boc-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: 85.0%

tert-butyl pyridin-2-yl carbonate (89985-91-1) + L-cystein, dicyclohexylammonium salt → 2-hydroxypyridin (142-08-5) + N-(tert-Butyloxycarbonyl)-L-cysteine (20887-95-0)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 10h; Ambient temperature;

DOI:10.1246/bcsj.58.3570

Reference yield: 84.0%

O-(tert-butyl) S-(pyridin-2-yl)carbonothioate (105678-24-8) + L-cystein, dicyclohexylammonium salt → 2-Sulfanylpyridine (2637-34-5,73018-10-7) + N-(tert-Butyloxycarbonyl)-L-cysteine (20887-95-0)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 12h; Ambient temperature;

DOI:10.1246/bcsj.58.3570

Reference yield:

N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine (76880-29-0) → 3-nitro-2-mercaptopyridine (38240-29-8) + N-(tert-Butyloxycarbonyl)-L-cysteine (20887-95-0)

Guidance literature:

With ethylenediaminetetraacetic acid; Tris buffer; papain; at 25 ℃; pH= 7.5;

DOI:10.1246/cl.1981.737

upstream raw materials:

N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine

tert-butyl pyridin-2-yl carbonate

O-(tert-butyl) S-(pyridin-2-yl)carbonothioate

Downstream raw materials:

N-(tert-butoxycarbonyl)-S-<(RS)-2-nitro-1-phenylethyl>-L-cysteine

N-Boc-S-all-trans-farnesyl-L-cysteine

N-tert-butoxycarbonyl-S-(4-dimethylamino)benzyl-L-cysteine

N-Boc-Cys(Pam-1)-OH

Refernces

• 1、 Matsueda, Rei,Kimura, Takahide,Kaiser, Emil Thomas,Matsueda, Gary R.. "3-NITRO-2-PYRIDINESULFENYL GROUP FOR PROTECTION AND ACTIVATION OF THE THIOL FUNCTION OF CYSTEINE". . p. 737 - 740. Retrieved 2007/10/02.