3-Benzylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid

Base Information

• Chemical Name: 3-Benzylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS No.: 5068-28-0
• Molecular Formula: C15H21NO4S
• Molecular Weight: 311.402
• Hs Code.: 29309090
• NSC Number: 164041
• Nikkaji Number: J1.094.897E
• ChEMBL ID: CHEMBL5196830
• Mol file: 5068-28-0.mol

Synonyms:223594-13-6;CHEMBL5196830;3-(benzylsulfanyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid;MFCD00065567;NSC164041;N-[(1,1-Dimethylethoxy)carbonyl]-S(phenylmethyl)-L-cysteine;SCHEMBL5853138;BDBM50604545;3-benzylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;AKOS005075897;NSC-164041;PD196892;SY057265;FT-0601990;FT-0629754;10P-093;L-Cysteine,1-dimethylethoxy)carbonyl]-S-(phenylmethyl)-;3-(benzylsulfanyl)-2-{[(tert-butoxy)carbonyl]amino}propanoicacid

Chemical Property of 3-Benzylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid

Chemical Property:

• Appearance/Colour: White solid.
• Vapor Pressure: 4.54E-10mmHg at 25°C
• Melting Point: 86-88 °C
• Refractive Index: -45 ° (C=1, AcOH)
• Boiling Point: 481.2 °C at 760 mmHg
• PKA: 3.58±0.10(Predicted)
• Flash Point: 244.8 °C
• PSA: 100.93000
• Density: 1.201 g/cm³
• LogP: 3.28860
• Storage Temp.: −20°C
• Solubility.: DMSO, Methanol
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 311.11912932
• Heavy Atom Count: 21
• Complexity: 348

Purity/Quality:

98%min ^*data from raw suppliers

N-Boc-S-benzyl-L-cysteine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CSCC1=CC=CC=C1)C(=O)O
• Uses: Boc-S-Benzyl-L-cysteine is used in peptide HIV1 enzymic synthesis

Technology Process of 3-Benzylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid

There total 19 articles about 3-Benzylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid 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: 100.0%

S-benzyl-L-cysteine (3054-01-1,25988-62-9) + di-tert-butyl dicarbonate (24424-99-5) → (2R)-3-benzylsulfanyl-2-tert-butoxycarbonylamino-propionic acid (5068-28-0)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 4h;

DOI:10.1002/jhet.5570320436

Reference yield:

C21H35NO5SSi → (2R)-3-benzylsulfanyl-2-tert-butoxycarbonylamino-propionic acid (5068-28-0)

Guidance literature:

With magnesium bromide ethyl etherate; In dichloromethane; at -20 - 22 ℃; for 3.5h;

DOI:10.1055/s-0034-1379004

Reference yield:

C24H41NO4SSi → (2R)-3-benzylsulfanyl-2-tert-butoxycarbonylamino-propionic acid (5068-28-0)

Guidance literature:

With potassium fluoride; In tetrahydrofuran; methanol; at 22 ℃; for 2h;

DOI:10.1055/s-0034-1379004

upstream raw materials:

S-benzyl-L-cysteine

tert-Butyl 4-nitrophenyl carbonate

N-(tert-butyloxycarbonyl) azide

di-tert-butyl dicarbonate

Downstream raw materials:

Boc-Cys(Bzl)-OEt

Boc-Cys(Bzl)-Tyr-OMe

BOCCys(Bzl)TyrIleOMe

BOCCys(Bzl)TyrIleOH

Refernces

• 1、 Suppo, Jean-Simon,De Sant'Ana, Danilo Pereira,Dias, Luiz Carlos,De Figueiredo, Renata Marcia,Campagne, Jean-Marc. "Efficient and practical procedure for the esterification of the free α-carboxylic acid of amino acid residues with β-(trimethylsilyl)ethoxymethyl chloride and triisopropylsilyl chloride". supporting information. p. 3075 - 3084. Retrieved 2015/01/08.
• 2、 Ageeva,Kurzeev,Kazankov. "Catalytic hydrolysis of α-amino esters in the presence of chiral palladacycles". . p. 548 - 552. Retrieved 2008/02/02.