N,N'-Dicarbobenzyloxy-L-cystine

Base Information

• Chemical Name: N,N'-Dicarbobenzyloxy-L-cystine
• CAS No.: 6968-11-2
• Molecular Formula: C22H24N2O8S2
• Molecular Weight: 508.573
• Hs Code.: 29309090
• European Community (EC) Number: 230-181-3
• NSC Number: 163310,154939,88480,20645
• DSSTox Substance ID: DTXSID10989832
• Nikkaji Number: J1.350.023A
• Mol file: 6968-11-2.mol

Synonyms:N,N'-Dicarbobenzyloxy-L-cystine;6968-11-2;(Z-Cys-OH);(Z-Cys-OH)2;NSC677484;BSBM7;N,N'-di-Cbz-L-cystine;N,N'-Dibenzyloxycarbonyl-L-cystine;di-Z-L-Cystine;Di-CBZ-l-cystine;N,N-di-Cbz-L-cystine;N-N-Bis-Z-L-cystine;N,N'-Bis-Cbz-L-cystine;SCHEMBL7354938;DTXSID10989832;PTRQEEVKHMDMCF-UHFFFAOYSA-N;NSC20645;NSC88480;EINECS 230-181-3;NSC 20645;NSC 88480;NSC-20645;NSC-88480;NSC154939;NSC163310;AKOS004907353;NSC 154939;NSC-154939;NSC-163310;FT-0656265;L-Cystine, N,N'-bis[(phenylmethoxy)carbonyl]-;N,N'-Bis[(benzyloxy)(hydroxy)methylidene]cystine;2-(benzyloxycarbonylamino)-3-[[2-(benzyloxycarbonylamino)-3-hydroxy-3-oxo-propyl]disulfanyl]propanoic acid

Chemical Property of N,N'-Dicarbobenzyloxy-L-cystine

Chemical Property:

• Vapor Pressure: 1.11E-24mmHg at 25°C
• Melting Point: 118-122 °C
• Refractive Index: -91 ° (C=8.8, AcOH)
• Boiling Point: 766.1 °C at 760 mmHg
• PKA: 3.15±0.10(Predicted)
• Flash Point: 417.1 °C
• PSA: 201.86000
• Density: 1.422 g/cm³
• LogP: 3.90880
• Storage Temp.: Store at RT.
• Solubility.: almost transparency in Methanol
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 15
• Exact Mass: 508.09740808
• Heavy Atom Count: 34
• Complexity: 613

Purity/Quality:

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

N,N''-Dibenzyloxycarbonyl-L-cystine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CSSCC(C(=O)O)NC(=O)OCC2=CC=CC=C2)C(=O)O
• Uses: N,N''-Dibenzyloxycarbonyl-L-cystine

Technology Process of N,N'-Dicarbobenzyloxy-L-cystine

There total 12 articles about N,N'-Dicarbobenzyloxy-L-cystine 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: 99.0%

L-cystine (56-89-3) + benzyl chloroformate (501-53-1,94274-21-2) → N,N'-bis(benzyloxycarbonyl)-L-cystine (6968-11-2)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃;

DOI:10.1139/V07-011

Reference yield: 95.0%

L-cystine (56-89-3) + benzyl pyridin-2-yl carbonate (96452-48-1) → N,N'-bis(benzyloxycarbonyl)-L-cystine (6968-11-2)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1246/bcsj.58.3570

Reference yield: 90.0%

N-benzyloxycarbonyl-L-cysteine (96289-13-3,53907-29-2) → N,N'-bis(benzyloxycarbonyl)-L-cystine (6968-11-2)

Guidance literature:

With [bis(acetoxy)iodo]benzene; In dichloromethane; for 0.0833333h; Ambient temperature;

DOI:10.1016/S0957-4166(00)82315-0

upstream raw materials:

L-cystine

benzyl chloroformate

N-benzyloxycarbonyl-L-cysteine

O-benzyl S-(pyridin-2-yl)carbonothioate

Downstream raw materials:

N,N'-bis[(phenylmethoxy)carbonyl]-L-cystine 1,1'-dimethyl ester

N,N'-bis(benzyloxycarbonyl)-L-cystine dibenzyl ester

(R,R)-N,N'-dibenzyloxycarbonyl-3,3'-dithiobis(2-aminopropionic acid)bis(methylamide)

Bis-N-benzyloxycarbonyl cystine di p-nitrophenyl ester

Refernces

• 1、 Schade, Markus,Merla, Beatrix,Lesch, Bernhard,Wagener, Markus,Timmermanns, Simone,Pletinckx, Katrien,Hertrampf, Torsten. "Highly Selective Sub-Nanomolar Cathepsin S Inhibitors by Merging Fragment Binders with Nitrile Inhibitors". supporting information. p. 11801 - 11808. Retrieved 2020/11/26.
• 2、 Kramer, Jessica R.,Deming, Timothy J.. "Glycopolypeptides with a redox-triggered helix-to-coil transition". supporting information; experimental part. p. 4112 - 4115. Retrieved 2012/04/10.