N-Biotinyl-N’-(N-Boc-S-trityl)cysteinyl Ethylenediamine

Base Information

• Chemical Name: N-Biotinyl-N’-(N-Boc-S-trityl)cysteinyl Ethylenediamine
• CAS No.: 508234-94-4
• Molecular Formula: C39H49N5O5S2
• Molecular Weight: 731.97
• Mol file: 508234-94-4.mol

Synonyms:[(1R)-2-[[2-[[5-[(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1-oxopentyl]amino]ethyl]amino]-2-oxo-1-[[(triphenylmethyl)thio]methyl]ethyl]carbamic Acid 1,1-Dimethylethyl Ester;N-Biotinyl-N’-(N-Boc-S-trityl)cysteinyl Ethylenediamine

Chemical Property of N-Biotinyl-N’-(N-Boc-S-trityl)cysteinyl Ethylenediamine

Chemical Property:

• PSA: 188.26000
• LogP: 7.39350
• Solubility.: Dichloromethane, DMSO, Methanol

Purity/Quality:

98%Min ^*data from raw suppliers

N-Biotinyl-N’-(N-Boc-S-trityl)cysteinylEthylenediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate for the preparation of N-Biotinyl-N?cysteinyl Ethylenediamine

Technology Process of N-Biotinyl-N’-(N-Boc-S-trityl)cysteinyl Ethylenediamine

There total 5 articles about N-Biotinyl-N’-(N-Boc-S-trityl)cysteinyl Ethylenediamine 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: 85.0%

N-tert-butyloxycarbonyl-S-trityl-L-cysteine (21947-98-8,87494-13-1) + (+)-biotinyl-2-aminoethan-1-aminium chloride (111822-45-8) → ((R)-1-{2-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethylcarbamoyl}-2-tritylsulfanyl-ethyl)-carbamic acid tert-butyl ester (508234-94-4)

Guidance literature:

N-tert-butyloxycarbonyl-S-trityl-L-cysteine; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; Inert atmosphere;

(+)-biotinyl-2-aminoethan-1-aminium chloride; In N,N-dimethyl-formamide; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1021/jacs.7b02952

Reference yield:

N-BOC-S-trityl-L-cysteine → (1-{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethylcarbamoyl}-2-tritylsulfanyl-ethyl)-carbamic acid tert-butyl ester (508234-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexylcarbodiimide / CH₂Cl₂ / 0.5 h / 20 °C

2: 379 mg / aq. Na₂CO₃ / acetonitrile / 10 h

With sodium carbonate; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile;

DOI:10.1016/S0968-0896(02)00311-5

Reference yield:

{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethyl}-carbamic acid tert-butyl ester (225797-46-6) → (1-{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethylcarbamoyl}-2-tritylsulfanyl-ethyl)-carbamic acid tert-butyl ester (508234-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 1 h / 20 °C

2: 379 mg / aq. Na₂CO₃ / acetonitrile / 10 h

With sodium carbonate; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0968-0896(02)00311-5

upstream raw materials:

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

N-biotinyl-1,2-diaminoethane

(+)-biotinyl-2-aminoethan-1-aminium chloride

{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethyl}-carbamic acid tert-butyl ester

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