Boc-cys(trt)-osu

Base Information

• Chemical Name: Boc-cys(trt)-osu
• CAS No.: 75179-29-2
• Molecular Formula: C₃₁H₃₂N₂O₆S
• Molecular Weight: 560.671
• DSSTox Substance ID: DTXSID401118115
• Mol file: 75179-29-2.mol

Synonyms:BOC-CYS(TRT)-OSU;75179-29-2;(2,5-dioxopyrrolidin-1-yl) (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-tritylsulfanylpropanoate;Boc-S-trityl-L-cysteine N-hydroxysuccinimide ester;SCHEMBL8357442;C31H32N2O6S;JIXAKJALBJDZTP-VWLOTQADSA-N;DTXSID401118115;2,5-dioxopyrrolidin-1-yl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[(triphenylmethyl)sulfanyl]propanoate;MFCD00235843;AKOS015841312;DS-9766;CS-0154514;D97598;(R)-2,5-dioxopyrrolidin-1-yl 2-(tert-butoxycarbonylamino)-3-(tritylthio)propanoate;N-alpha-t-Butyloxycarbonyl-S-trityl-L-cysteine succinimidyl ester (Boc-L-Cys(Trt)-OSu);2,5-DIOXOPYRROLIDIN-1-YL (2R)-2-[(TERT-BUTOXYCARBONYL)AMINO]-3-[(TRIPHENYLMETHYL)SULFANYL]PROPANOATE;N-[(1,1-Dimethylethoxy)carbonyl]-S-(triphenylmethyl)-L-cysteine 2,5-dioxo-1-pyrrolidinyl ester

Chemical Property of Boc-cys(trt)-osu

Chemical Property:

• PSA: 127.31000
• LogP: 5.54100
• Storage Temp.: Store at 0°C
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 560.19810792
• Heavy Atom Count: 40
• Complexity: 838

Purity/Quality:

98.5% ^*data from raw suppliers

Boc-Cys(Trt)-OSu 95+% ^*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(CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)ON4C(=O)CCC4=O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)ON4C(=O)CCC4=O

Technology Process of Boc-cys(trt)-osu

There total 4 articles about Boc-cys(trt)-osu 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%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-tert-butyloxycarbonyl-S-trityl-L-cysteine (21947-98-8,87494-13-1) → 2-tert-butoxycarbonylamino-3-(tritylsulfanyl)propionic acid 2,5-dioxopyrrolidin-1-yl ester (87242-61-3,75179-29-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/open.201700191

Reference yield:

N-tert-butyloxycarbonyl-S-trityl-L-cysteine (21947-98-8,87494-13-1) → 2-tert-butoxycarbonylamino-3-(tritylsulfanyl)propionic acid 2,5-dioxopyrrolidin-1-yl ester (87242-61-3,75179-29-2)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In acetonitrile;

Reference yield:

S-trityl-L-cysteine (2799-07-7) → 2-tert-butoxycarbonylamino-3-(tritylsulfanyl)propionic acid 2,5-dioxopyrrolidin-1-yl ester (87242-61-3,75179-29-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / water / 24 h / 20 °C

1.2: pH 2

2.1: dicyclohexyl-carbodiimide / acetonitrile / 14 h / 0 - 20 °C / Inert atmosphere

With dicyclohexyl-carbodiimide; sodium hydroxide; In water; acetonitrile;

DOI:10.1016/j.ejmech.2012.02.018

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

N-tert-butyloxycarbonyl-S-trityl-L-cysteine

triphenylmethyl alcohol

S-trityl-L-cysteine

Downstream raw materials:

Fmoc-Lys[N-Boc-Cys(Trt)]-OH

{1-[2-(3,4-dihydroxyphenyl)ethyl]carbamoyl-2-(tritylsulfanyl)ethyl}carbamic acid tert-butyl ester

2-amino-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(tritylsulfanyl)propionamide

3-(3,4-dihydroxyphenyl)-N-{1-[2-(3,4-dihydroxyphenyl)ethylcarbamoyl]-2-(tritylsulfanyl)ethyl}acrylamide

Refernces

• 1、 Gao,Ieritano,Chen,Dias,Rousseau,Bénard,Seimbille. "Two bifunctional desferrioxamine chelators for bioorthogonal labeling of biovectors with zirconium-89". supporting information. p. 5102 - 5106. Retrieved 2018/07/29.
• 2、 Silvia, Vertuani,Baldisserotto, Anna,Scalambra, Emanuela,Malisardi, Gemma,Durini, Elisa,Manfredini, Stefano. "Novel molecular combination deriving from natural aminoacids and polyphenols: Design, synthesis and free-radical scavenging activities". experimental part. p. 383 - 392. Retrieved 2012/07/28.