N,N'-Di-Boc-(L)-cystine-dimethyl Ester

Base Information

• Chemical Name: N,N'-Di-Boc-(L)-cystine-dimethyl Ester
• CAS No.: 77826-55-2
• Molecular Formula: C18H32 N2 O8 S2
• Molecular Weight: 468.593
• European Community (EC) Number: 691-150-1
• DSSTox Substance ID: DTXSID90456799
• Nikkaji Number: J1.102.501C
• Wikidata: Q82279373
• Mol file: 77826-55-2.mol

Synonyms:N,N'-Di-Boc-(L)-cystine-dimethyl Ester;77826-55-2;(Boc-L-Cys-Ome)2;methyl (2R)-3-[[(2R)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]disulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;N,N'-Bis[(tert-butyloxy)carbonyl]-L-cystine dimethyl ester;Dimethyl 3,3'-disulfanediyl(2R,2'R)-bis(2-((tert-butoxycarbonyl)amino)propanoate);SCHEMBL9679571;DTXSID90456799;YYJNNBRJCNKRNJ-RYUDHWBXSA-N;MFCD09757603;N,N-Di-boc-(l)-cystine-dimethyl ester;F88132;N,N'-Bis(tert-butoxycarbonyl)cystine dimethyl ester;N,N'-bis-(t-butyloxycarbonyl)-l-cystine dimethyl ester;N,N inverted exclamation mark -Di-Boc-(L)-cystine-dimethyl Ester;methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-{[(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxy-3-oxopropyl]disulfanyl}propanoate

Chemical Property of N,N'-Di-Boc-(L)-cystine-dimethyl Ester

Chemical Property:

• Melting Point: 118-120°C
• Boiling Point: 583.7±50.0 °C(Predicted)
• PKA: 10.33±0.46(Predicted)
• PSA: 179.86000
• Density: 1.213±0.06 g/cm3(Predicted)
• LogP: 3.28220
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 15
• Exact Mass: 468.16000833
• Heavy Atom Count: 30
• Complexity: 550

Purity/Quality:

98% ^*data from raw suppliers

N,N’-Di-Boc-(L)-cystine-dimethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CSSCC(C(=O)OC)NC(=O)OC(C)(C)C)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CSSC[C@@H](C(=O)OC)NC(=O)OC(C)(C)C)C(=O)OC
• Uses: N,N’-Di-Boc-(L)-cystine-dimethyl Ester (cas# 77826-55-2) is a compound useful in organic synthesis.

Technology Process of N,N'-Di-Boc-(L)-cystine-dimethyl Ester

There total 22 articles about N,N'-Di-Boc-(L)-cystine-dimethyl 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: 100.0%

N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester (172749-96-1) → N,N'-bis(tert-butoxy)carbonyl-L-cystine dimethyl ester (77826-55-2)

Guidance literature:

With dihydrogen peroxide; sodium iodide; In ethyl acetate; at 20 ℃; for 0.5h;

DOI:10.1021/acs.orglett.6b01023

Reference yield: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + L-cystine dimethyl ester dihydrochloride (32854-09-4) → N,N'-bis(tert-butoxy)carbonyl-L-cystine dimethyl ester (77826-55-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; water; at 0 - 20 ℃; for 24h;

DOI:10.1021/acs.joc.1c02608

Reference yield: 98.0%

Nα-tert-butoxycarbonyl-S-allyloxycarbonylaminomethyl-L-cysteine methyl ester (160978-32-5) → N,N'-bis(tert-butoxy)carbonyl-L-cystine dimethyl ester (77826-55-2)

Guidance literature:

N^α-tert-butoxycarbonyl-S-allyloxycarbonylaminomethyl-L-cysteine methyl ester; With tri-n-butyl-tin hydride; acetic acid; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; at 20 ℃; for 0.5h;

With iodine; In tetrachloromethane;

DOI:10.1016/S0040-4020(99)00322-1

upstream raw materials:

di-tert-butyl dicarbonate

L-cystine dimethyl ester dihydrochloride

S-methyl-L-cysteine methyl ester hydrochloride salt

N-tert-butyloxycarbonyl-S-(4-methoxybenzyl)cysteine methyl ester

Downstream raw materials:

methyl (6S,9R,14R)-6-benzyl-14-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)-9-(methoxycarbonyl)-2,2-dimethyl-4,7-dioxo-3-oxa-11,12-dithia-5,8-diazapentadecan-15-oate

L-cystine dimethyl ester

(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(((2S,3R)-2-(cyclopropylmethyl)-6,6,6-trifluoro-3-(((S)-9-fluoro-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)carbamoyl)hexanamido)thio)propanoate

(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(((2S,3R)-6,6,6-trifluoro-3-(((S)-5-(3-fluorophenyl)-9-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)carbamoyl)-2-(3,3,3-trifluoropropyl)hexanamido)thio)propanoate

Refernces

• 1、 Yano De Albuquerque, Danilo,Teixeira, Wystan K. O.,Sacramento, Manoela Do,Alves, Diego,Santi, Claudio,Schwab, Ricardo S.. "Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source". supporting information. p. 595 - 605. Retrieved 2022/01/12.
• 2、 -. "A green disulfide synthesis method". Paragraph 0052-0054. . Retrieved 2022/01/08.