BOC-CYS(TBU)-OH

Base Information

• Chemical Name: BOC-CYS(TBU)-OH
• CAS No.: 56976-06-8
• Molecular Formula: C12H23NO4S
• Molecular Weight: 277.385
• Mol file: 56976-06-8.mol

Synonyms:T-BUTYLOXYCARBONYL-S-T-BUTYL-L-CYSTEINE;N-ALPHA-T-BUTYLOXYCARBONYL-S-T-BUTYL-L-CYSTEINE;N-ALPHA-T-BUTOXYCARBONYL-S-T-BUTYL-L-CYSTEINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-S-TERT-BUTYL-L-CYSTEINE;BOC-(S)-T-BUTYL-L-CYS;BOC-S-T-BUTYL-L-CYSTEINE;BOC-(S)-TERT-BUTYL-L-CYS;BOC-(R)-2-AMINO-3-(S-T-BUTYLTHIO)BUTANOIC ACID

Chemical Property of BOC-CYS(TBU)-OH

Chemical Property:

• PSA: 100.93000
• LogP: 2.88690
• Storage Temp.: Store at 0°C

Purity/Quality:

98%Min ^*data from raw suppliers

Boc-S-tert-butyl-L-cysteine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Boc-Cys(tBu)-OH, is a Cystine derivative, used in various chemical synthesis and peptide chemistry.

Technology Process of BOC-CYS(TBU)-OH

There total 2 articles about BOC-CYS(TBU)-OH 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: 78.0%

N-(tert-butyloxycarbonyl) azide (1070-19-5) + S-tert-Butyl-N-acetyl-L-cysteine hydrochloride (2481-09-6) → N-(Carbo-tert-butoxy)-S-tert-butyl-L-cysteine (56976-06-8,872211-02-4)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 48h; Ambient temperature;

DOI:10.1021/jo00322a024

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (R)-S-tert-butylcysteine (2481-10-9,300583-35-1) → N-(Carbo-tert-butoxy)-S-tert-butyl-L-cysteine (56976-06-8,872211-02-4)

Guidance literature:

With sodium hydroxide; In acetonitrile;

DOI:10.1039/c4ra10936h

Reference yield: 97.1%

N-(Carbo-tert-butoxy)-S-tert-butyl-L-cysteine (56976-06-8,872211-02-4) → L-Cysteine (52-90-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; diphenyl sulfide; In trifluoroacetic acid; at 0 ℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;

DOI:10.1248/cpb.35.3447

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

S-tert-Butyl-N-acetyl-L-cysteine hydrochloride

di-tert-butyl dicarbonate

(R)-S-tert-butylcysteine

Downstream raw materials:

L-Cysteine

(R)-2-((R)-2-Acetylsulfanylmethyl-3-phenyl-propionylamino)-3-tert-butylsulfanyl-propionic acid methyl ester

(R)-2-((S)-2-Acetylsulfanylmethyl-3-phenyl-propionylamino)-3-tert-butylsulfanyl-propionic acid methyl ester

Refernces

• 1、 Pastuszak, Juliusz Jacek,Chimiak, Andrzej. "tert-Butyl group as thiol protection in peptide synthesis". . p. 1868 - 1873. Retrieved 2007/10/02.