N-BOC-S-BENZYL-(L)-CYSTEINE-METHYL ESTER

Base Information

• Chemical Name: N-BOC-S-BENZYL-(L)-CYSTEINE-METHYL ESTER
• CAS No.: 55478-08-5
• Molecular Formula: C16H23NO4S
• Molecular Weight: 325.429
• Hs Code.: 2930909090
• Mol file: 55478-08-5.mol

Synonyms:Boc-Cys(SBzl)-OMe;Boc-Cys(Bn)-OMe;N-Boc-S-benzyl-L-cysteine Methyl Ester;

Chemical Property of N-BOC-S-BENZYL-(L)-CYSTEINE-METHYL ESTER

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 462.9±45.0 °C(Predicted)
• PKA: 10.83±0.46(Predicted)
• PSA: 89.93000
• Density: 1.143±0.06 g/cm3(Predicted)
• LogP: 3.37700
• Solubility.: Acetone, Chloroform, Dichloromethane, Ethyl Acetate

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Used in peptide HIV1 enzymic synthesis

Technology Process of N-BOC-S-BENZYL-(L)-CYSTEINE-METHYL ESTER

There total 9 articles about N-BOC-S-BENZYL-(L)-CYSTEINE-METHYL ESTER 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: 93.0%

methanol (67-56-1) + (2R)-3-benzylsulfanyl-2-tert-butoxycarbonylamino-propionic acid (5068-28-0) → N-[(1,1-dimethylethoxy)-carbonyl]-S-(phenylmethyl)-L-cysteine methyl Ester (55478-08-5)

Guidance literature:

With thionyl chloride; di-tert-butyl dicarbonate; In methanol; at 0 - 20 ℃; for 7h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.0c01771

Reference yield: 82.0%

N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester (172749-96-1) + benzyl bromide (100-39-0) → N-[(1,1-dimethylethoxy)-carbonyl]-S-(phenylmethyl)-L-cysteine methyl Ester (55478-08-5)

Guidance literature:

N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester; With sodium methylate; In methanol; at -10 ℃; for 0.166667h;

benzyl bromide; In methanol; at 20 ℃;

DOI:10.1002/chem.202002868

Reference yield: 70.0%

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) + benzoic acid (65-85-0,8013-63-6) → Boc-Cys(Bzl)-OMe (55478-08-5)

Guidance literature:

With N-Bromosuccinimide; benzyltriethylammonium tetrathiomolybdate; triphenylphosphine; In chloroform; at 28 ℃; for 2h;

DOI:10.1002/ejoc.200900956

upstream raw materials:

diazomethane

Boc-Cys(Bzl)-OH

methanol

N-tert-butyloxycarbonyl-L-serine methyl ester

Downstream raw materials:

N-tert-butoxycarbonyl-S-benzyl-(R)-cysteinol

S-benzyl-L-cysteine methyl ester hydrochloride

N-(tert-butyloxycarbonyl)-S-benzyl-L-cysteinyl-D-valine benzyl ester

Refernces

• 1、 Debia, Natalí P.,Rodríguez, Juan J.P.,da Silveira, Carolina H.,Chaves, Otavio A.,Iglesias, Bernardo A.,Rodembusch, Fabiano S.,Lüdtke, Diogo S.. "Synthesis and photophysics of benzazole based triazoles with amino acid-derived pendant units. Multiparametric optical sensors for BSA and CT-DNA in solution". . . Retrieved 2020/04/27.
• 2、 Di Gioia,Barattucci,Bonaccorsi,Leggio,Minuti,Romio,Temperini,Siciliano. "Deprotection/reprotection of the amino group in α-amino acids and peptides. A one-pot procedure in [Bmim][BF4] ionic liquid". . p. 2678 - 2686. Retrieved 2014/01/06.