N,N''-[DITHIOBIS(O-PHENYLENECARBONYL)]BIS-L-ISOLEUCINE

Base Information

• Chemical Name: N,N''-[DITHIOBIS(O-PHENYLENECARBONYL)]BIS-L-ISOLEUCINE
• CAS No.: 182149-25-3
• Molecular Formula: C26H32 N2 O6 S2
• Molecular Weight: 0
• Mol file: 182149-25-3.mol

Synonyms:N,N’’-[DITHIOBIS(O-PHENYLENECARBONYL)]BIS-L-ISOLEUCINE

Chemical Property of N,N''-[DITHIOBIS(O-PHENYLENECARBONYL)]BIS-L-ISOLEUCINE

Chemical Property:

• PSA: 183.40000
• LogP: 5.72600

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N,N''-[DITHIOBIS(O-PHENYLENECARBONYL)]BIS-L-ISOLEUCINE

There total 6 articles about N,N''-[DITHIOBIS(O-PHENYLENECARBONYL)]BIS-L-ISOLEUCINE 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: 91.0%

(2S,3S)-2-{2-[2-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-3-methyl-pentanoic acid tert-butyl ester (181861-32-5) → (2S,3S)-2-{[2-[[2-(1S,2S)-[(1-carboxy-2-methylbutyl)carbamoyl]phenyl]dithio]benzoyl]amino}-3-methylpentanoic acid (182149-25-3)

Guidance literature:

With trifluoroacetic acid; for 18h; Ambient temperature;

DOI:10.1021/jm960253w

Reference yield: 75.0%

2,2'-dithiodibenzoic acid dichloride (19602-82-5) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) → (2S,3S)-2-{[2-[[2-(1S,2S)-[(1-carboxy-2-methylbutyl)carbamoyl]phenyl]dithio]benzoyl]amino}-3-methylpentanoic acid (182149-25-3)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 60 - 65 ℃; for 2h; Large scale;

DOI:10.1021/op9701191

Reference yield: 65.0%

→ (2S,3S)-2-{[2-[[2-(1S,2S)-[(1-carboxy-2-methylbutyl)carbamoyl]phenyl]dithio]benzoyl]amino}-3-methylpentanoic acid (182149-25-3)

Guidance literature:

upstream raw materials:

(2S,3S)-2-{2-[2-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-3-methyl-pentanoic acid tert-butyl ester

2,2'-dithiodibenzoic acid dichloride

2,2'-dithiobenzoic acid

L-Isoleucin-tert-butylester

Downstream raw materials:

(2S,3S)-3-methyl-2-(3-oxo-3H-benzo[d]isothiazol-2-yl)pentanoic acid

Refernces

• 1、 Fiore, Phillip J.,Puls, Timothy P.,Walker, Jonathan C.. "Development and pilot-scale demonstration of a process for inhibitors of the HIV nucleocapsid protein, NCp7". . p. 151 - 156. Retrieved 2013/09/08.
• 2、 Loo, Joseph A.,Holler, Tod P.,Sanchez, Joseph,Gogliotti, Rocco,Maloney, Lisa,Reily, Michael D.. "Biophysical characterization of zinc ejection from HIV nucleocapsid protein by anti-HIV 2,2'-dithiobis[benzamides] and benzisothiazolones". . p. 4313 - 4320. Retrieved 2007/10/03.